(r)-1-Cbz-2-cyanopyrrolidine

Base Information

• Chemical Name: (r)-1-Cbz-2-cyanopyrrolidine
• CAS No.: 620601-77-6
• Molecular Formula: C13H14N2O2
• Molecular Weight: 230.266
• Hs Code.: 2933990090
• European Community (EC) Number: 674-832-3
• DSSTox Substance ID: DTXSID40466186
• Nikkaji Number: J1.783.505J
• Wikidata: Q72516123
• Mol file: 620601-77-6.mol

Synonyms:620601-77-6;(r)-1-cbz-2-cyanopyrrolidine;(R)-1-CBZ-2-CYANO-PYRROLIDINE;benzyl (2R)-2-cyanopyrrolidine-1-carboxylate;(r)-benzyl 2-cyanopyrrolidine-1-carboxylate;MFCD06796619;(r)-1-n-cbz-2-cyano-pyrrolidine;SCHEMBL1437419;DTXSID40466186;AUVGQGIWVNDVSL-GFCCVEGCSA-N;AKOS015836813;AS-38676;A8583;Benzyl (R)-2-cyanopyrrolidine-1-carboxylate;CS-0146417;Q-102180;(r)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (r)-1-Cbz-2-cyanopyrrolidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 403.618 °C at 760 mmHg
• PKA: -5.02±0.40(Predicted)
• Flash Point: 197.902 °C
• PSA: 53.33000
• Density: 1.208 g/cm³
• LogP: 2.24908
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.105527694
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

97% ^*data from raw suppliers

(R)-1-Cbz-2-cyanopyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)OCC2=CC=CC=C2)C#N
• Isomeric SMILES: C1C[C@@H](N(C1)C(=O)OCC2=CC=CC=C2)C#N

Technology Process of (r)-1-Cbz-2-cyanopyrrolidine

There total 2 articles about (r)-1-Cbz-2-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: 64.0%

(2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester (62937-47-7,58274-22-9) → (+)-(R)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester (620601-77-6)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1039/b414742a

Reference yield:

Z-D-proline (6404-31-5) → (+)-(R)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester (620601-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1-hydroxybenzotriazole; EDCI / tetrahydrofuran / 0.5 h / 20 °C

1.2: 68 percent / aq. NH₃ / tetrahydrofuran / 24 h / 20 °C

2.1: 64 percent / p-TsCl; pyridine / CH₂Cl₂ / 72 h / 20 °C

With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b414742a

Reference yield: 100.0%

(+)-(R)-2-cyano-pyrrolidine-1-carboxylic acid benzyl ester (620601-77-6) → (2R)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (839711-73-8)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 90 ℃; for 16h;

upstream raw materials:

(2R)-2-carbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Z-D-proline

Downstream raw materials:

(2R)-2-(1H-tetrazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

(R)-5-(pyrrolidin-2-yl)-1H-tetrazole

(R)-benzyl 2-(1-(4-chlorobenzyl)-1H-tetrazol-5-yl)pyrrolidine-1-carboxylate

C₂₀H₂₀ClN₅O₂