Methyl N-boc-L-proline-4-ene

Base Information

• Chemical Name: Methyl N-boc-L-proline-4-ene
• CAS No.: 83548-46-3
• Molecular Formula: C11H17 N O4
• Molecular Weight: 227.26
• Hs Code.: 2933990090
• European Community (EC) Number: 845-280-2
• DSSTox Substance ID: DTXSID60472209
• Nikkaji Number: J1.236.158K
• Mol file: 83548-46-3.mol

Synonyms:83548-46-3;METHYL N-BOC-L-PROLINE-4-ENE;(S)-1-tert-Butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;N-Boc-L-proline-4-ene Methyl Ester;1-O-tert-butyl 2-O-methyl (2S)-2,3-dihydropyrrole-1,2-dicarboxylate;1-tert-butyl 2-methyl (2S)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate;(S)-2,3-DIHYDRO-PYRROLE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER;MFCD09261402;METHYLN-BOC-L-PROLINE-4-ENE;SCHEMBL14182270;DTXSID60472209;WGCPPYJWSDCBNC-QMMMGPOBSA-N;AKOS025287056;(S)-2,3-Dihydro-1H-pyrrole-1,2-dicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester;AS-38042;EN300-185799;A923209;2S)-2,3-Dihydro-1H-pyrrole-1,2-dicarboxylic Acid 1-(1,1-Dimethylethyl) 2-Methyl Ester

Chemical Property of Methyl N-boc-L-proline-4-ene

Chemical Property:

• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.491
• Boiling Point: 299.2°C at 760 mmHg
• Flash Point: 134.8°C
• PSA: 55.84000
• Density: 1.148g/cm³
• LogP: 1.62040
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 316

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-L-proline-4-eneMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CCC1C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N1C=CC[C@H]1C(=O)OC
• Uses: N-Boc-L-proline-4-ene Methyl Ester is a L-proline derivative used in the preparation of intermediates for dipeptidyl peptidase (DPP) IV inhibitors

Technology Process of Methyl N-boc-L-proline-4-ene

There total 4 articles about Methyl N-boc-L-proline-4-ene 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: 5.0%

(2S,4R)-4-Methylsulfanylthiocarboxyoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (74844-92-1) → 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (83548-46-3)

Guidance literature:

at 170 - 180 ℃; for 6h; under 12 Torr;

Reference yield:

diethylamino-sulfur trifluoride (38078-09-0) + 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (83548-46-3) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

diethylamino-sulfur trifluoride; 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate; In dichloromethane; at 5 ℃; for 12h;

With sodium hydrogencarbonate; In dichloromethane; water; Product distribution / selectivity;

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) + 2,2-difluoro-1,3-dimethyl-imidazolidine (220405-40-3) → N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate (83548-46-3) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate; 2,2-difluoro-1,3-dimethyl-imidazolidine; In toluene; at 75 ℃; for 4h;

With potassium hydroxide; In water; toluene; Product distribution / selectivity;

upstream raw materials:

(2S,4R)-4-Methylsulfanylthiocarboxyoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

L-4-hydroxyproline methyl ester hydrochloride

diethylamino-sulfur trifluoride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

(1S,3S,5S)-2-tert-butyl 3-methyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

(3S)-3-((tert-butyldiphenylsilyloxy)methyl)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane

Refernces

• 1、 Schumacher, Kelly K.,Jiang, Jianjun,Joullie, Madeleine M.. "Synthetic studies toward astins A, B and C. Efficient syntheses of cis- 3,4-dihydroxyprolines and (-)-(3S,4R)-dichloroproline esters". . p. 47 - 53. Retrieved 2007/10/03.