L-Proline, 4-(cyanomethyl)-, cis-

Base Information

• Chemical Name: L-Proline, 4-(cyanomethyl)-, cis-
• CAS No.: 119595-96-9
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.169
• DSSTox Substance ID: DTXSID80469095
• Mol file: 119595-96-9.mol

Synonyms:119595-96-9;(2S,4R)-4-(cyanomethyl)pyrrolidine-2-carboxylic Acid;L-Proline, 4-(cyanomethyl)-, cis- (9CI);L-PROLINE, 4-(CYANOMETHYL)-, CIS-;DTXSID80469095;(2S,4R)-4-(cyanomethyl)pyrrolidine-2-carboxylicAcid

Chemical Property of L-Proline, 4-(cyanomethyl)-, cis-

Chemical Property:

• PSA: 73.12000
• LogP: 0.29158
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 154.074227566
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC1C(=O)O)CC#N
• Isomeric SMILES: C1[C@@H](CN[C@@H]1C(=O)O)CC#N

Technology Process of L-Proline, 4-(cyanomethyl)-, cis-

There total 14 articles about L-Proline, 4-(cyanomethyl)-, cis- 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: 66.0%

(2S,4R)-4-(cyanomethyl)-N-(9-(9-phenylfluorenyl))proline tert-butyl ester (119595-92-5) → (2S,4R)-4-(cyanomethyl)proline (119595-96-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 16h;

DOI:10.1021/jo00269a022

Reference yield:

(2S)-4-cyanomethylenepyrrolidine-1,2-dicarboxylic acid dibenzyl ester (903518-04-7) → (2S,4R)-4-(cyanomethyl)proline (119595-96-9) + (2S,4S)-4-(cyanomethyl)proline (119595-95-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water;

DOI:10.1021/jo060210f

Reference yield:

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3) → (2S,4R)-4-(cyanomethyl)proline (119595-96-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / DMSO; (CF₃CO)2O; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / -78 - 20 °C

3.1: H₂ / Pd/C

With hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo060210f

upstream raw materials:

(2S,4R)-4-(cyanomethyl)-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

(2S)-4-cyanomethyl-2,5-dihydropyrrole-1,2-dicarboxylic acid dibenzyl ester

(2S)-4-cyanomethylenepyrrolidine-1,2-dicarboxylic acid dibenzyl ester

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester