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Cas Database

69610-41-9

69610-41-9

Identification

  • Product Name:N-BOC-L-Prolinal

  • CAS Number: 69610-41-9

  • EINECS:627-548-9

  • Molecular Weight:199.25

  • Molecular Formula: C10H17NO3

  • HS Code:29339900

  • Mol File:69610-41-9.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-formyl-, 1,1-dimethylethyl ester, (S)-;(S)-1-Boc-2-formylpyrrolidine;(S)-1-tert-Butoxycarbonylpyrrolidine-2-carboxaldehyde;(S)-2-Formylpyrrolidine-1-carboxylic acid tert-butyl ester;1,1-Dimethylethyl(2S)-2-formyl-1-pyrrolidinecarboxylate;Boc-L-prolinal;Boc-prolinal;N-(tert-Butoxycarbonyl)-L-prolinal;N-(tert-Butoxycarbonyl)prolinal;N-(tert-Butyloxycarbonyl)-(S)-prolinal;N-Boc-L-prolinal;N-tert-Butoxycarbonyl-(S)-prolinal;tert-Butoxycarbonyl-L-prolinal;tert-Butyl(2S)-2-formyl-1-pyrrolidinecarboxylate;tert-Butyl(2S)-2-formylpyrrolidine-1-carboxylate;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

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  • Manufacture/Brand:Usbiological
  • Product Description:Boc-L-prolinal
  • Packaging:500mg
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:N-Boc-L-Prolinal
  • Packaging:50mg
  • Price:$ 45
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Boc-L-prolinal
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Boc-L-prolinal
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N-Boc-L-prolinal
  • Packaging:5 g
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  • Manufacture/Brand:SynChem
  • Product Description:(S)-Boc-pyrrolidine-2-carbaldehyde 95+%
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  • Manufacture/Brand:SynChem
  • Product Description:(S)-Boc-pyrrolidine-2-carbaldehyde 95+%
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  • Manufacture/Brand:SynChem
  • Product Description:(S)-Boc-pyrrolidine-2-carbaldehyde 95+%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Boc-L-prolinal 97%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:(S)-tert-Butyl 2-formylpyrrolidine-1-carboxylate 95%
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Relevant articles and documentsAll total 178 Articles be found

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo

, p. 8303 - 8332 (2021/06/30)

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor

Grudzień, Krzysztof,Noga?, Wojciech,Szczepaniak, Grzegorz,Grela, Karol

supporting information, (2021/02/26)

Commercially available N-Boc protected L-proline can be efficiently converted into a chiral, bidentate, aminoalkyl N-heterocyclic carbene ligand precursor in high yield (50% total after 4 steps) without column chromatography purification at any moment. The developed synthetic path includes: (1) redox step leading to an aldehyde, (2) imine condensation and in situ reduction to 1,2-diamine; (3) heterocyclization; (3) removal of the protecting group. Instant separation of Cu traces after the key Stahl oxidation at gram-scale was facilitated by the use of bis(isocyanide) scavenger, SnatchCat, forming insoluble, easy to remove RNC:→[Cu] complexes that allowed usto obtain crude intermediate suitably pure for next steps without tedious purification.

NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG

-

Paragraph 0235-0236, (2021/05/14)

PROBLEM TO BE SOLVED: To provide: a method for producing a connected body; a method for using the connected body in the production of a uniform conjugate; and a method for applying the conjugate in the treatment of cancer, infectious diseases, and autoimmune diseases. SOLUTION: A novel connected body is provided that includes a 2,3-di-substituted succinic acid group or a 2-mono-substituted or 2,3-di-substituted fumaric acid or maleic acid (trans (E)- or cis (Z)-butenedioic acid) group for conjugating 2 or more compounds/cytotoxic agents per connected body with a cell-binding molecule by specifically bridge-linking to a pair of thiol on the cell-binding molecule. The connected body is exemplified by the following general formula. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Process route upstream and downstream products

Process route

(S)-N-(tert-butoxycarbonyl)proline methyl ester
59936-29-7

(S)-N-(tert-butoxycarbonyl)proline methyl ester

Conditions
Conditions Yield
With diisobutylaluminium hydride; In toluene; at -60 ℃; for 2h;
98%
With diisobutylaluminium hydride; In toluene; at -60 ℃; for 0.5h;
97%
With diisobutylaluminium hydride;
95%
With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h;
93%
With diisobutylaluminium hydride; In toluene; at -78 ℃;
91%
With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2h;
90%
With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃; for 2h;
90%
With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
72%
With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -60 ℃; for 0.5h;
With diisobutylaluminium hydride; In toluene; at -78 ℃;
With diisobutylaluminum hydride; In hexane; at -60 ℃; for 0.5h;
68.2 g
With diisobutylaluminium hydride; In hexane; toluene; for 0.5h;
With diisobutylaluminium hydride; In toluene; at -78 ℃;
With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃;
With potassium hydrogensulfate; diisobutylaluminium hydride; Yield given. Multistep reaction; 1.) toluene, -78 deg C, 1.5 h, 2.) toluene, from -78 deg C to RT;
With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.0833333h;
With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
With diisobutylaluminium hydride; In toluene;
With diisobutylaluminium hydride; In toluene; at -78 ℃; for 3.5h;
Multi-step reaction with 2 steps
1: 97 percent / LiBH4 / tetrahydrofuran / 20 °C
2: 99 percent / TEMPO; NaClO; NaBr / NaHCO3 / CH2Cl2; H2O
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium borohydride; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water;
Multi-step reaction with 2 steps
1: 85 percent / NaBH4; LiCl; EtOH / tetrahydrofuran
2: 81 percent / SO3*pyridine; DMSO; Et3N / CH2Cl2
With sodium tetrahydroborate; pyridine-SO3 complex; ethanol; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: LiBH4; trimethylborate
With lithium borohydride; Trimethyl borate; 1: Reduction / 2: Oxidation;
Multi-step reaction with 2 steps
1: 92.4 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 4 h / Ambient temperature
2: oxalyl chloride / CH2Cl2; dimethylsulfoxide / 0.33 h / -78 °C
With sodium tetrahydroborate; oxalyl dichloride; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: 81 percent / LiCl, NaBH4 / ethanol; tetrahydrofuran / 16 h / Ambient temperature
2: SO3*pyridine, Et3N / dimethylsulfoxide; CH2Cl2 / 0.17 h / Ambient temperature
With sodium tetrahydroborate; pyridine-SO3 complex; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: 92 percent / LiBH4
2: 100 percent / (COCl)2/DMSO / triethylamine
With lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; In triethylamine;
Multi-step reaction with 2 steps
1: 94 percent / LiCl, sodium borohydride, EtOH / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 19.5 h
2: 95 percent / sulfur trioxide-pyridine complex, DMSO, Et3N / CH2Cl2 / 0.17 h / 10 - 20 °C
With sodium tetrahydroborate; ethanol; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
With diisobutylaluminium hydride;
(S)-N-(tert-butoxycarbonyl)proline methyl ester; With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 4h;
With methanol; In dichloromethane; toluene; at -78 - 20 ℃;
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C
2.2: -78 - 0 °C
With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C / Inert atmosphere
2.2: -78 - 0 °C / Inert atmosphere
With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
With diisobutylaluminium hydride; In toluene; at -60 ℃; Inert atmosphere;
With diisobutylaluminium hydride; In deuteromethanol;
With diisobutylaluminium hydride;
With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 3h;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
2: Dess-Martin periodane / dichloromethane / 20 °C
With lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere
With lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2: |Dess-Martin Oxidation;
tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate
115186-37-3

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate

Conditions
Conditions Yield
With lithium aluminium tetrahydride; at 0 ℃; for 0.25h;
100%
With lithium aluminium tetrahydride; In diethyl ether; at -10 ℃; for 0.5h;
96%
With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Ambient temperature;
89%
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;
86%
With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃;
82%
With lithium aluminium tetrahydride; In diethyl ether; at -5 ℃; for 0.333333h;
78%
With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃; for 2h;
78%
tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;
With sodium hydroxide; water; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;
74%
With lithium aluminium tetrahydride; In diethyl ether;
73%
With lithium aluminium tetrahydride; In tetrahydrofuran; at -15 ℃;
With lithium aluminium tetrahydride; In diethyl ether;
With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.25h;
With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;
tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate; With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.75h;
With methanol; In dichloromethane; at -78 - 0 ℃;
With lithium aluminium tetrahydride; In diethyl ether; at -15 ℃;
With lithium aluminium tetrahydride; In tetrahydrofuran; at -15 - 0 ℃; for 1h;
N-(tert-butoxycarbonyl)-L-prolinol
69610-40-8

N-(tert-butoxycarbonyl)-L-prolinol

Conditions
Conditions Yield
With oxalyl dichloride; dimethyl sulfoxide; In triethylamine;
100%
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide;
100%
With Dess-Martin periodane; tert-butyl alcohol; In dichloromethane; Ambient temperature;
99%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide; sodium hydrogencarbonate; In dichloromethane; water;
99%
With [bis(acetoxy)iodo]benzene; BF4(1-)*C19H32N6O2(1+); In dichloromethane; at 20 ℃; for 0.166667h;
98%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I)tetrafluoroborate; In acetonitrile; for 21h; Heating;
98%
With 1,10-Phenanthroline; potassium tert-butylate; copper(l) chloride; dibenzyl azodicarboxylate; oxygen; In fluorobenzene; Heating;
97%
With di-tert-butyl-diazodicarboxylate; potassium tert-butylate; oxygen; 1,10-Phenanthroline; copper(l) chloride; In fluorobenzene; Heating;
97%
With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h;
97.6%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 0 - 20 ℃;
96%
With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 16h;
96%
With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 10 - 20 ℃; for 0.166667h;
95%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
95%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;
With triethylamine; In dichloromethane; at -78 ℃;
95%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
95%
With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2.16667h;
95%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;
With triethylamine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
94%
N-(tert-butoxycarbonyl)-L-prolinol; With dimethyl sulfoxide; triethylamine; at 5 - 10 ℃; for 0.25h;
With sulfur trioxide pyridine complex; at 0 ℃; for 2h;
94%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 1.08333h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 0.75h; Inert atmosphere;
94%
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; for 2h; Ambient temperature;
93%
With Dess-Martin periodane; In dichloromethane; for 2h; Ambient temperature;
92%
With sodium hypochlorite; TEMPO; sodium hydrogencarbonate; sodium bromide; In dichloromethane; at 0 ℃; for 1h;
92%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; chlorine; sodium hydrogencarbonate; sodium bromide; In dichloromethane; at 0 ℃; for 1h;
92%
With sodium hypochlorite; sodium hydrogencarbonate; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; at 0 ℃; for 1h;
92%
With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane;
92%
N-(tert-butoxycarbonyl)-L-prolinol; With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 50 ℃; for 16h;
With 1,4-bis(3-isocyanopropyl)piperazine; In dichloromethane; at 20 ℃; for 0.166667h;
91%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 0 - 20 ℃;
88.8%
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; at 7 - 8 ℃; for 2.5h;
87%
With Dess-Martin periodane; In dichloromethane; at 20 ℃;
87%
With sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; In dichloromethane; water; at 0 ℃;
86%
With phosgene; dimethyl sulfoxide; triethylamine;
85%
With pivaloyl chloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;
85%
With Oxone; sodium ortho-iodobenzenesulfonate; sodium sulfate; In ethyl acetate; at 70 ℃; for 8h; Inert atmosphere;
85%
With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h;
85%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 3h;
85%
With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
83%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile;
83%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; for 0.5h; Inert atmosphere; Reflux;
83%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; In water; ethyl acetate; toluene; at 0 ℃; for 0.166667h;
82%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
82%
With pyridine-SO3 complex; dimethyl sulfoxide; triethylamine; In dichloromethane;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide; at 20 ℃; for 3.16667h; Cooling with ice;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide; at 20 ℃; for 2.5h; Cooling with ice;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide; at 20 ℃; for 3.16667h; Cooling with ice;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h; Cooling with ice;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide; at 20 ℃; for 2.5h;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h;
With sulfur trioxide pyridine complex; at 20 ℃; for 2.5h;
81%
N-(tert-butoxycarbonyl)-L-prolinol; With triethylamine; In dimethyl sulfoxide; for 0.25h;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide; at 20 ℃; for 3.16667h; Cooling with ice;
81%
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 20 ℃; for 3.41667h; Cooling with ice;
81%
With oxygen; potassium carbonate; CuCl*Phen; dibenzyl azodicarboxylate; In fluorobenzene; at 80 ℃;
80%
With pyridinium chlorochromate; In dichloromethane; for 3h;
80%
With 4 A molecular sieve; P(p-CH3OC6H4)3; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 1h;
80%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
80%
With pyridium chlorochromate;
79%
With pyridine-SO3 complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 1h;
77%
With pyridinium chlorochromate; In dichloromethane; at 20 ℃; Molecular sieve;
76%
With pyridinium chlorochromate; In dichloromethane; at 20 ℃; Molecular sieve;
76%
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; at 20 ℃;
75%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; Heating;
74%
With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;
71%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.25h;
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
58.8%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; for 0.75h; Cooling with dry ice;
With triethylamine; In dichloromethane; at 0 ℃; for 1h; Cooling with dry ice;
55.4%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; for 0.75h; Cooling with ice; Inert atmosphere;
With triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
55.4%
With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at -10 - 20 ℃; for 16h;
55%
With pyridinium chlorochromate; In hexane; dichloromethane; ethyl acetate;
52.9%
N-(tert-butoxycarbonyl)-L-prolinol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.333333h;
With triethylamine; In dichloromethane; water; dimethyl sulfoxide; at 25 ℃; for 0.0833333h;
52%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere; Sealed tube;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
50.7%
With lithium tetrafluoroborate; tert.-butylnitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; Reagent/catalyst; Inert atmosphere; Reflux;
42%
With sodium carbonate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 6h;
36%
With 4 A molecular sieve; acetic acid; pyridinium chlorochromate; In dichloromethane; water; for 2h; Ambient temperature;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Multistep reaction; 1) THF, 2h, -70 deg C 2) 15 min, -70 deg C;
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; for 0.166667h; Ambient temperature;
With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction; 1) CH2Cl2, -63 deg C, 30 min, 2) up to r.t., 30 min;
With pyridine-SO3 complex; triethylamine; In dichloromethane; dimethyl sulfoxide; for 0.166667h; Ambient temperature;
With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 0.333333h;
With sulfur trioxide pyridine complex; In dimethyl sulfoxide;
With 4-methyl-morpholine; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -65 - 0 ℃;
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; 1.) 0 deg C, 1 h; 2.) 0-10 deg C, 2.5 h;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -63 ℃; Yield given;
In dichloromethane; Swern oxidation;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 0.583333h;
With Dess-Martin periodane; In dichloromethane; at 20 ℃;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -50 ℃; for 0.5h;
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium hypochlorite; sodium bromide; sodium hydrogencarbonate; In ethyl acetate; toluene; at 0 ℃; for 1.25h;
With Dess-Martin periodane; In dichloromethane;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -63 ℃;
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; at 5 ℃; for 2.5h;
With pyridine; sulfur trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at -5 ℃; for 5h;
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 20 ℃; for 0.25h;
70 % Turnov.
With dipyridinium dichromate;
With oxalyl dichloride; TEA; dimethyl sulfoxide; In dichloromethane; at -78 - 0 ℃;
With dimethyl sulfoxide; triethylamine; In dichloromethane; at -63 ℃;
N-(tert-butoxycarbonyl)-L-prolinol
69610-40-8

N-(tert-butoxycarbonyl)-L-prolinol

Conditions
Conditions Yield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
99%
pyrrolidine-1,2-dicarboxylic acid 1-<i>tert</i>-butyl ester 2-(4,6-dimethoxy-[1,3,5]triazin-2-yl) ester

pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(4,6-dimethoxy-[1,3,5]triazin-2-yl) ester

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol; at 20 ℃; for 3h;
82%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
1-(tert-butoxycarbonyl)-L-proline; With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 5h; Inert atmosphere;
76%
With molecular sieve; sodium acetate;
Multi-step reaction with 3 steps
1: CH2Cl2
3: 73 percent / LiAlH4 / diethyl ether
With lithium aluminium tetrahydride; In diethyl ether; dichloromethane;
Multi-step reaction with 2 steps
1: 93 percent / K2CO3 / dimethylformamide
2: 91 percent / DIBAH / toluene / -78 °C
With diisobutylaluminium hydride; potassium carbonate; In N,N-dimethyl-formamide; toluene;
Multi-step reaction with 2 steps
1: 92 percent / borane dimethylsulfide complex / tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight
2: 93 percent / Et3N, sulfur trioxide pyridine complex / dimethylsulfoxide / 2 h / Ambient temperature
With dimethylsulfide borane complex; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: BH3*Me2S / tetrahydrofuran / 2.5 h / Heating
2: SO3*pyridine, Et3N / dimethylsulfoxide / 1.) 0 deg C, 1 h; 2.) 0-10 deg C, 2.5 h
With pyridine-SO3 complex; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: 90 percent / BH3-SMe2 / tetrahydrofuran
2: 85 percent / (COCl2), DMSO, Et3N
With phosgene; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: 76 percent / B2H6*THF / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) r.t., 1 h
2: 87 percent / SO3*pyridine, Et3N / dimethylsulfoxide / 2.5 h / 7 - 8 °C
With pyridine-SO3 complex; B2H6-THF; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 3 steps
1: N-methylmorpholine / CH2Cl2 / 1 h / -15 °C
2: N-methylmorpholine
3: LiAlH4 / tetrahydrofuran / -15 °C
With 4-methyl-morpholine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: 82 percent / BOP, DIEA / CH2Cl2
2: 89 percent / AlLiH4 / tetrahydrofuran / 1 h / Ambient temperature
With lithium aluminium tetrahydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 3 steps
1: Et3N / -10 °C
2: CH2Cl2 / 2 h / Ambient temperature
3: 96 percent / LiAlH4 / diethyl ether / 0.5 h / -10 °C
With lithium aluminium tetrahydride; triethylamine; In diethyl ether; dichloromethane;
Multi-step reaction with 3 steps
1: dicyclohexylcarbodiimide (DCC), dimethylaminopyridine (DMAP) / CH2Cl2 / 0 - 20 °C
2: 92.4 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 4 h / Ambient temperature
3: oxalyl chloride / CH2Cl2; dimethylsulfoxide / 0.33 h / -78 °C
With dmap; sodium tetrahydroborate; oxalyl dichloride; dicyclohexyl-carbodiimide; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: BH3*Me2S / tetrahydrofuran
2: pyridine*SO3 / dimethylsulfoxide
With dimethylsulfide borane complex; sulfur trioxide pyridine complex; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: 98 percent / BH3*SMe2 / tetrahydrofuran / 0.75 h / Heating
2: 1) DMSO, (COCl)2, 2) iPr2NEt / 1) CH2Cl2, -63 deg C, 30 min, 2) up to r.t., 30 min
With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: 1) hydroxybenzotriazole monohydrate, dicyclohexylcarbodiimide, 2) triethylamine / 1) CH2Cl2, 0 deg C, 2) overnight, RT
2: 78 percent / LiAlH4 / diethyl ether / 0.33 h / -5 °C
With lithium aluminium tetrahydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether;
Multi-step reaction with 2 steps
1: 90 percent / DBU
2: 95 percent / DIBAL-H
With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
Multi-step reaction with 2 steps
1: BH3*SMe2 / tetrahydrofuran / 1.) 0 deg C, 2.) reflux, 1 h
2: pyridinium chlorochromate (PCC), acetic acid, 4A molecular sieves / H2O; CH2Cl2 / 2 h / Ambient temperature
With dimethylsulfide borane complex; 4 A molecular sieve; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water;
Multi-step reaction with 2 steps
1: 73 percent / BH3*Me2S / tetrahydrofuran / 20 h
2: 1) oxalyl chloride, DMSO 2) Et3N / 1) THF, 2h, -70 deg C 2) 15 min, -70 deg C
With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / 0 - 10 °C
1.2: 0 °C
2.1: sodium hydrogencarbonate; sodium hypochlorite; TEMPO; sodium bromide / dichloromethane / 1 h / 0 °C
With sodium hypochlorite; TEMPO; dimethylsulfide borane complex; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / 0 - 10 °C
1.2: 0 °C
2.1: sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; chlorine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 1 h / 0 °C
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dimethylsulfide borane complex; chlorine; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
With lithium aluminium tetrahydride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 18 h / 0 - 10 °C
1.2: 0 °C
2.1: sodium hydrogencarbonate; sodium hypochlorite; sodium bromide / 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 1 h / 0 °C
With sodium hypochlorite; dimethylsulfide borane complex; sodium hydrogencarbonate; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide
2: diisobutylaluminium hydride / deuteromethanol
With diisobutylaluminium hydride; potassium carbonate; In deuteromethanol; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 6 h / Inert atmosphere
2: tetrahydrofuran / 2 h / Inert atmosphere
With borane-THF; In tetrahydrofuran; 2: |Swern Oxidation;
Multi-step reaction with 2 steps
1: diborane / tetrahydrofuran / 3 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With Dess-Martin periodane; diborane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 °C / Inert atmosphere
2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C
With dimethylsulfide borane complex; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Sealed tube
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere; Sealed tube
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: diborane / tetrahydrofuran / 3 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With Dess-Martin periodane; diborane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide
2: lithium aluminium tetrahydride / diethyl ether / -15 °C
With lithium aluminium tetrahydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In diethyl ether; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: dichloromethane / 1 h / 0 °C / Schlenk technique; Inert atmosphere
2: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Schlenk technique; Inert atmosphere
With diisobutylaluminium hydride; In dichloromethane;
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h
2.2: 3.17 h / 20 °C / Cooling with ice
With borane-THF; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h
2.2: 2.5 h / 20 °C / Cooling with ice
With borane-THF; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 20 °C
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.25 h / -78 °C
2.2: 20 °C
With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran
2: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide
With sodium tetrahydroborate; boron trifluoride diethyl etherate; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 0 - 20 °C
2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite solution; sodium bromide / dichloromethane; water / 0 °C
With sodium hypochlorite solution; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; In tetrahydrofuran; dichloromethane; water;
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1.08 h / -78 °C / Inert atmosphere
2.2: 0.75 h / 20 °C / Inert atmosphere
With borane-THF; oxalyl dichloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1.1: borane; tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h
2.2: 3.17 h / 20 °C / Cooling with ice
With tetrahydrofuran; borane; triethylamine; In dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0.2 h / 0 - 20 °C
2: Dess-Martin periodane / dichloromethane / 0.2 h / 0 - 20 °C / Inert atmosphere
With lithium aluminium tetrahydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 5.83 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2.17 h / 20 °C
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2: |Dess-Martin Oxidation;
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran
2: oxalyl dichloride; dimethyl sulfoxide / dichloromethane
With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h / Cooling with ice
2.2: 2.5 h / 20 °C
With borane-THF; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1.1: isobutyl chloroformate; triethylamine / dichloromethane / 0.5 h / -7 °C
1.2: 16 h / -7 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
With lithium aluminium tetrahydride; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 - 0 °C
With lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 °C / Reflux
2: sodium carbonate; pyridinium chlorochromate / dichloromethane / 6 h / 20 °C
With dimethylsulfide borane complex; sodium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1.1: borane / tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h
2.2: 2.5 h / 20 °C
With borane; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 1.5 h / 0 °C
2.1: triethylamine / dimethyl sulfoxide / 0.25 h
2.2: 3.17 h / 20 °C / Cooling with ice
With borane-THF; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 - 20 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(actonitrile)copper(I) hexafluorophosphate; [2,2]bipyridinyl; 1-methyl-1H-imidazole / acetonitrile / 16 h / 50 °C
2.2: 0.17 h / 20 °C
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dimethylsulfide borane complex; In tetrahydrofuran; acetonitrile;
Multi-step reaction with 2 steps
1: diborane / tetrahydrofuran / 1.5 h / 0 °C
2: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 3.42 h / 20 °C / Cooling with ice
With sulfur trioxide pyridine complex; triethylamine; diborane; In tetrahydrofuran; dimethyl sulfoxide;
Boc-Pro-SEt
459142-82-6

Boc-Pro-SEt

Conditions
Conditions Yield
With triethylsilane; palladium on activated charcoal; In acetone; at 20 ℃;
87%
(2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
135097-23-3,575452-35-6,125347-83-3

(2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Conditions
Conditions Yield
With diisobutylaluminium hydride; at -78 ℃;
90%
With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 1h;
63%
With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃; for 3h;
carbon monoxide
201230-82-2

carbon monoxide

N-(tert-butoxycarbonyl)-2,3-dihydropyrrole
73286-71-2

N-(tert-butoxycarbonyl)-2,3-dihydropyrrole

tert-butoxycarbonyl-D-prolinal
73365-02-3,117625-90-8

tert-butoxycarbonyl-D-prolinal

Conditions
Conditions Yield
With hydrogen; carbonylhydridetris(triphenylphosphine)rhodium(I); (-)-DIPHOL; In benzene; at 52 ℃; for 192h; under 25857.4 Torr; Yield given. Title compound not separated from byproducts;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4,59433-50-0

1-(tert-butoxycarbonyl)-L-proline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: BH3*THF
2: PDC
With dipyridinium dichromate; borane-THF;
Multi-step reaction with 2 steps
1: 99 percent / BH3*Me2S / tetrahydrofuran / 20 °C
2: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 °C
With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;
Multi-step reaction with 2 steps
1: 81 percent / TBTU; Et3N / dimethylformamide / 6 h / 20 °C
2: 78 percent / LiAlH4 / tetrahydrofuran / 2 h / -10 °C
With lithium aluminium tetrahydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: 88 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 14 h / 0 - 12 °C
2: LiAlH4 / diethyl ether / 0.25 h / 0 °C
With lithium aluminium tetrahydride; diethyl cyanophosphonate; triethylamine; In diethyl ether; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: 17.11 g / HOBt; DMAP; EDAC*HCl / CH2Cl2 / 16 h / 0 - 20 °C
2: DIBAL / toluene; diethyl ether / 3 h / -78 °C
With dmap; diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In diethyl ether; dichloromethane; toluene;
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2 / 0.17 h / 0 °C
2: Et3N / CH2Cl2
3: 87 percent / Et3SiH / 10 percent Pd/C / acetone / 20 °C
With triethylsilane; triethylamine; palladium on activated charcoal; In dichloromethane; acetone;
Multi-step reaction with 2 steps
1: 94 percent / BH3*Me2S
With dimethylsulfide borane complex; 2: Swern oxidation;

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