Benzyl (2S)-2-(chloromethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Benzyl (2S)-2-(chloromethyl)pyrrolidine-1-carboxylate
• CAS No.: 61350-66-1
• Molecular Formula: C13H16ClNO2
• Molecular Weight: 253.729
• Hs Code.: 2933990090
• European Community (EC) Number: 675-929-3
• DSSTox Substance ID: DTXSID60558193
• Wikidata: Q76423674
• Mol file: 61350-66-1.mol

Synonyms:61350-66-1;(S)-1-N-Cbz-2-chloromethyl-pyrrolidine;(S)-benzyl 2-(chloromethyl)pyrrolidine-1-carboxylate;Benzyl (2S)-2-(chloromethyl)pyrrolidine-1-carboxylate;(s)-1-cbz-2-chloromethyl-pyrrolidine;(s)-2-chloromethyl-pyrrolidine-1-carboxylic acid benzyl ester;DTXSID60558193;MFCD06796608;AKOS017344709;(s)-1-n-cbz-2-chloromethylpyrrolidine;AC-9235;AM101020;AS-38170;CS-0171380;A13109;EN300-214317;(S)-benzyl2-(chloromethyl)pyrrolidine-1-carboxylate;Benzyl (S)-2-(chloromethyl)pyrrolidine-1-carboxylate

Chemical Property of Benzyl (2S)-2-(chloromethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 8.7E-06mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 373.9°C at 760 mmHg
• Flash Point: 179.9°C
• PSA: 29.54000
• Density: 1.205g/cm³
• LogP: 2.96430
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 253.0869564
• Heavy Atom Count: 17
• Complexity: 254

Purity/Quality:

97% ^*data from raw suppliers

(S)-1-Cbz-2-chloromethyl-pyrrolidine 95% ^*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)CCl
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)OCC2=CC=CC=C2)CCl

Technology Process of Benzyl (2S)-2-(chloromethyl)pyrrolidine-1-carboxylate

There total 4 articles about Benzyl (2S)-2-(chloromethyl)pyrrolidine-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: 94.0%

(S)-2-(chloromethyl)pyrrolidine hydrochloride (35120-33-3) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-(chloromethyl)-1-pyrrolidinecarboxylic acid phenylmethyl ester (61350-66-1,1187932-05-3)

Guidance literature:

With triethylamine; at 0 ℃;

DOI:10.1016/j.bmcl.2003.11.032

Reference yield:

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → (S)-2-(chloromethyl)-1-pyrrolidinecarboxylic acid phenylmethyl ester (61350-66-1,1187932-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / SOCl₂; HCl / CHCl₃

2: 94 percent / Et₃N / 0 °C

With hydrogenchloride; thionyl chloride; triethylamine; In chloroform;

DOI:10.1016/j.bmcl.2003.11.032

Reference yield:

N-Cbz-Prolinol (6216-63-3) → (S)-2-(chloromethyl)-1-pyrrolidinecarboxylic acid phenylmethyl ester (61350-66-1,1187932-05-3)

Guidance literature:

With phosgene; triethylamine; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 1h;

DOI:10.1002/anie.201107877

upstream raw materials:

(S)-2-(chloromethyl)pyrrolidine hydrochloride

benzyl chloroformate

(S)-1-Pyrrolidin-2-yl-methanol

N-Cbz-Prolinol

Downstream raw materials:

(2S)-(-)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate

(2R)-(+)-phenylmethyl 2-vinylpyrrolidine-1-carboxylate

4-{2-[2-(2R-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile

(R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester