(S)-Tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (S)-Tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate
• CAS No.: 115186-37-3
• Molecular Formula: C12H22 N2 O4
• Molecular Weight: 258.318
• Hs Code.: 2933990090
• European Community (EC) Number: 854-922-0
• DSSTox Substance ID: DTXSID70350867
• Nikkaji Number: J1.016.344G
• Wikidata: Q72510466
• Mol file: 115186-37-3.mol

Synonyms:115186-37-3;Boc-Pro-NMe(OMe);(S)-TERT-BUTYL 2-(METHOXY(METHYL)CARBAMOYL)PYRROLIDINE-1-CARBOXYLATE;N-(tert-Butoxycarbonyl)-L-proline N'-methoxy-N'-methylamide;tert-butyl (2S)-2-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate;Boc-Pro-N(Me)OMe;SCHEMBL903492;DTXSID70350867;(S)-2-(N-Methoxy-N-methylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester;MFCD00209555;AKOS008864944;AT35354;Boc-L-proline N,O-dimethyl hydroxamide;FS-4734;N-methyl-N-methoxy-(Boc-proline)-amide;EN300-1590070;(S)-1-Boc-2-[methoxy(methyl)carbamoyl]pyrrolidine;J-003260;1-(tert-Butoxycarbonyl)-N-methyl-N-methoxyprolinamide;N-alpha-t-Butyloxycarbonyl-N-methyl-N-methyloxy-L-proline amide;(S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate;N-(tert-Butoxycarbonyl)-L-proline N'-methoxy-N'-methylamide, 98%;tert-butyl (2S)-2-(methoxy-methylcarbamoyl)pyrrolidine-1-carboxylate;TERT-BUTYL (S)-2-(METHOXY(METHYL)CARBAMOYL)PYRROLIDINE-1-CARBOXYLATE;(S)-2-(Methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid, 2-[(methoxymethylamino)carbonyl]-, 1,1-dimethylethyl ester, (2S)-

Chemical Property of (S)-Tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate

Chemical Property:

• Refractive Index: n20/D 1.471(lit.)
• Boiling Point: 326.2°Cat760mmHg
• Flash Point: 151.1°C
• PSA: 59.08000
• Density: 1.131g/cm³
• LogP: 1.34360
• Storage Temp.: Store at 0°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 258.15795719
• Heavy Atom Count: 18
• Complexity: 325

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L-proline N,O-dimethylhydroxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)N(C)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)N(C)OC
• Uses: α-Amino Weinreb amide.

Technology Process of (S)-Tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate

There total 18 articles about (S)-Tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate 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: 99.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate (115186-37-3)

Guidance literature:

1-(tert-butoxycarbonyl)-L-proline; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.25h;

N,O-dimethylhydroxylamine*hydrochloride; In dichloromethane; at 20 ℃;

Reference yield: 98.2%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + N,0-dimethylhydroxylamine (1117-97-1) → tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate (115186-37-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In chloroform;

DOI:10.1002/hc.10195

Reference yield: 89.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate (115186-37-3)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -20 ℃; for 0.666667h;

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

N,O-dimethylhydroxylamine*hydrochloride

(S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

C₁₅H₂₅NO₅

Downstream raw materials:

(S)-2-(2,2,3,3,3-Pentafluoro-propionyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

2-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

2(S)-(4-phenylbutyryl)pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-2-(4-methylbenzoyl)pyrrolidine

Refernces

• 1、 Huy, Peter,Schmalz, Hans-Guenther. "Practical one-pot double functionalizations of proline". . p. 954 - 960. Retrieved 2011.
• 2、 Mascarin, Alba,Valverde, Ibai E.,Vomstein, Sandra,Mindt, Thomas L.. "1,2,3-Triazole Stabilized Neurotensin-Based Radiopeptidomimetics for Improved Tumor Targeting". . p. 2143 - 2152. Retrieved 2015.
• 3、 Garsi, Jean-Baptiste,Sernissi, Lorenzo,Vece, Vito,Hanessian, Stephen,McCracken, Alison N.,Simitian, Grigor,Edinger, Aimee L.. "In search of constrained FTY720 and phytosphingosine analogs as dual acting anticancer agents targeting metabolic and epigenetic pathways". . p. 217 - 242. Retrieved 2018.
• 4、 Woo, Jacqueline C. S.,Fenster, Erik,Dake, Gregory R.. "A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides". . p. 8984 - 8986. Retrieved 2004.
• 5、 Balboni, Gianfranco,Marastoni, Mauro,Merighi, Stefania,Borea, Pier Andrea,Tomatis, Roberto. "Synthesis and activity of 3-pyridylamine ligands at central nicotinic receptors". . p. 979 - 988. Retrieved 2000.
• 6、 Kondoh, Azusa,Ojima, Rihaku,Terada, Masahiro. "Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines". supporting information. p. 7894 - 7899. Retrieved 2021/10/20.
• 7、 Bihel, Frédéric,Bricard, Jacques,Garnier, Delphine,Gizzi, Patrick,Leloire, Maeva,Mohr, Julie,Schmitt, Martine,Schneider, Séverine,Tang, Shuang-Qi. "Diastereoselective Synthesis of Nonplanar 3-Amino-1,2,4-oxadiazine Scaffold: Structure Revision of Alchornedine". . p. 15347 - 15359. Retrieved 2020/11/30.