Benzyl 2-cyanopyrrolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl 2-cyanopyrrolidine-1-carboxylate
• CAS No.: 119020-06-3
• Molecular Formula: C13H14 N2 O2
• Molecular Weight: 230.266
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70564326
• Mol file: 119020-06-3.mol

Synonyms:119020-06-3;1-Cbz-2-cyanopyrrolidine;benzyl 2-cyanopyrrolidine-1-carboxylate;1-N-CBZ-2-CYANOPYRROLIDINE;1-Z-2-cyanopyrrolidine;2-CYANO-PYRROLIDINE-1-CARBOXYLIC ACID BENZYL ESTER;1-Pyrrolidinecarboxylic acid, 2-cyano-, phenylmethyl ester;MFCD04115334;1-N-Cbz-2-cycanopyrrolidine;SCHEMBL1437422;(R)-1-Cbz-2-cyano-pyrrolidin;DTXSID70564326;AUVGQGIWVNDVSL-UHFFFAOYSA-N;BCP33974;BCP33975;AB1316;AKOS015912258;AB22868;AB29502;AB91757;CS-11942;SY033856;CS-0146416;EN300-190201;A804152;J-004055

Chemical Property of Benzyl 2-cyanopyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 403.6±45.0 °C(Predicted)
• PKA: -5.02±0.40(Predicted)
• PSA: 53.33000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.24908
• Storage Temp.: Sealed in dry,Room Temperature
• 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:

98%min ^*data from raw suppliers

Benzyl2-cyanopyrrolidine-1-carboxylate ^*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

Technology Process of Benzyl 2-cyanopyrrolidine-1-carboxylate

There total 14 articles about Benzyl 2-cyanopyrrolidine-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: 90.0%

3-oxo-1λ3-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile (172876-96-9) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → (±)-benzyl 2-cyanopyrrolidine-1-carboxylate (119020-06-3)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; cesium benzoate; In tetrahydrofuran; at 20 ℃; for 4h; Solvent; Concentration; Wavelength; Catalytic behavior; Mechanism; Molecular sieve; Irradiation;

DOI:10.1039/c6sc04907a

Reference yield: 89.0%

3-oxo-1λ3-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile (172876-96-9) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → 2-tetrahydrofuran-2-carbonitrile (14631-43-7) + (±)-benzyl 2-cyanopyrrolidine-1-carboxylate (119020-06-3)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; cesium benzoate; In tetrahydrofuran; at 20 ℃; Solvent; Catalytic behavior; Irradiation; Molecular sieve;

DOI:10.1039/c6sc04907a

Reference yield: 82.0%

2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester (93188-01-3,58274-22-9) → (±)-benzyl 2-cyanopyrrolidine-1-carboxylate (119020-06-3)

Guidance literature:

In pyridine; dichloromethane; at -10 ℃; for 2.66667h;

upstream raw materials:

2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester

3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile

N-Benzyloxycarbonyl-L-proline

bromocyane

Downstream raw materials:

2-ethoxycarbonimidoyl-pyrrolidine-1-carboxylic acid benzyl ester hydrochloride

Refernces

• 1、 Wakaki, Takayuki,Sakai, Kentaro,Enomoto, Takafumi,Kondo, Mio,Masaoka, Shigeyuki,Oisaki, Kounosuke,Kanai, Motomu. "C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis". supporting information. p. 8051 - 8055. Retrieved 2018/06/15.
• 2、 Le Vaillant, Franck,Waser, Jér?me. "Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents". . p. 226 - 230. Retrieved 2017/06/27.