(4S)-1-Boc-4-benzyl-L-proline

Base Information

• Chemical Name: (4S)-1-Boc-4-benzyl-L-proline
• CAS No.: 83623-78-3
• Molecular Formula: C17H23 N O4
• Molecular Weight: 305.37
• Hs Code.: 2933990090
• European Community (EC) Number: 675-717-0
• DSSTox Substance ID: DTXSID80451894
• Nikkaji Number: J1.912.271I
• Wikidata: Q76416445
• Mol file: 83623-78-3.mol

Synonyms:83623-78-3;(4S)-1-Boc-4-benzyl-L-proline;(2S,4S)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4S)-4-benzyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,4S)-4-Benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid;MFCD07784045;(2S,4S)-1-Boc-4-benzylpyrrolidine-2-carboxylicacid;SCHEMBL6183348;DTXSID80451894;trans-4-Benzyl-N-Boc-L-proline;JPNHKKRLLDYCIZ-KBPBESRZSA-N;(2s,4s)-4-benzyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;AKOS016010091;AS-36765;CS-0171719;A13695;EN300-6491872;Z3378135535;(cis)-1-[(1,1-Dimethylethoxy)carbonyl]-4-(phenylmethyl)-L-proline;(2S,4S)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;(2s,4s)-4-benzylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;4alpha-Benzylpyrrolidine-1,2alpha-dicarboxylic acid 1-tert-butyl ester;rac-(2R,4R)-4-benzyl-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;1233518-18-7

Chemical Property of (4S)-1-Boc-4-benzyl-L-proline

Chemical Property:

• Vapor Pressure: 8.32E-09mmHg at 25°C
• Refractive Index: 1.55
• Boiling Point: 447.9°C at 760 mmHg
• Flash Point: 224.7°C
• PSA: 66.84000
• Density: 1.185g/cm³
• LogP: 2.87720
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

97% ^*data from raw suppliers

(2S,4S)-4-Benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)CC2=CC=CC=C2

Technology Process of (4S)-1-Boc-4-benzyl-L-proline

There total 10 articles about (4S)-1-Boc-4-benzyl-L-proline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethyl (2S,4S)-N-BOC-4-benzylprolinate (170947-82-7) → (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline (83623-78-3,158459-13-3)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.03.120

Reference yield:

4-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (153074-95-4,158459-13-3) + (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline (83623-78-3,158459-13-3)

Guidance literature:

4-benzyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH₂PO₄ buffer; sodium hypochlorite; In water; acetonitrile; at 45 ℃; for 24h; pH=6.6; Title compound not separated from byproducts;

DOI:10.1021/jo034214l

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline (83623-78-3,158459-13-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aqueous Na₂CO₃ / tetrahydrofuran; dioxane / 18 h

2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C

3.1: 11.96 g / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.33 h / Cooling

4.1: 78 percent / TEA; DMAP / CH₂Cl₂

5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

6.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

6.2: 70 percent / tetrahydrofuran / 20 °C

7.1: 95 percent / Raney-Ni; hydrogen / methanol / 18 h / 20 °C / 760 Torr

8.1: TBAF / tetrahydrofuran / 6 h / 20 °C

8.2: NaClO₂; TEMPO; aqueous NaH₂PO₄ buffer / NaClO / H₂O; acetonitrile / 24 h / 45 °C / pH 6.6

With 4-methyl-morpholine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; TEA; trichloroisocyanuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; nickel; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; 6.2: Wittig reaction;

DOI:10.1021/jo034214l

upstream raw materials:

ethyl (2S,4S)-N-BOC-4-benzylprolinate

di-tert-butyl dicarbonate

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid