(R)-1-N-Cbz-3-cyanopyrrolidine

Base Information

• Chemical Name: (R)-1-N-Cbz-3-cyanopyrrolidine
• CAS No.: 329012-80-8
• Molecular Formula: C13H14 N2 O2
• Molecular Weight: 230.26
• Hs Code.: 2933990090
• Mol file: 329012-80-8.mol

Synonyms:3-Cyano-1-pyrrolidinecarboxylic acid phenylmethyl ester

Chemical Property of (R)-1-N-Cbz-3-cyanopyrrolidine

Chemical Property:

• PSA: 53.33000
• Density: 1.20
• LogP: 2.10658
• Storage Temp.: 2-8°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

(R)-Benzyl3-Cyanopyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-1-N-Cbz-3-cyanopyrrolidine

There total 6 articles about (R)-1-N-Cbz-3-cyanopyrrolidine 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: 80.0%

potassium cyanide (151-50-8) + benzyl (3S)-3-(p-tolylsulfonyloxy)pyrrolidine-1-carboxylate (158654-83-2) → 3-cyanopyrrolidine-1-carboxylic acid benzyl ester (329012-80-8)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃; for 4h;

DOI:10.1016/S0960-894X(97)00311-9

Reference yield:

(+/-)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester (188846-99-3) → (R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid (192214-06-5) + (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid (192214-00-9) + 3-cyanopyrrolidine-1-carboxylic acid benzyl ester (329012-80-8) + (+)-(S)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester (193693-69-5)

Guidance literature:

With ethylenediaminetetraacetic acid; In phosphate buffer; at 30 ℃; for 18h; pH=8.00; Title compound not separated from byproducts.;

DOI:10.1002/adsc.200700040

Reference yield:

(S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester (100858-32-0) → 3-cyanopyrrolidine-1-carboxylic acid benzyl ester (329012-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.41 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

2: 72 percent / dimethylsulfoxide / 4 h / 90 °C

With dmap; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/b301507f

upstream raw materials:

potassium cyanide

benzyl (3S)-3-(p-tolylsulfonyloxy)pyrrolidine-1-carboxylate

(S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester

benzyl chloroformate

Downstream raw materials:

(R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid

Refernces

• 1、 Cardillo, Giuliana,Gentilucci, Luca,Tolomelli, Alessandra,Calienni, Maria,Qasem, Ahmed R.,Spampinato, Santi. "Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline". . p. 1498 - 1502. Retrieved 2007/10/03.
• 2、 Klein, Scott I.,Czekaj, Mark,Molino, Bruce F.,Valeria, Chu. "Constrained β-alanine based GpIIb/IIIa antagonists". . p. 1773 - 1778. Retrieved 2007/10/03.