(R)-Ethyl pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (R)-Ethyl pyrrolidine-2-carboxylate
• CAS No.: 96163-72-3
• Molecular Formula: C7H13 N O2
• Molecular Weight: 143.186
• Hs Code.: 2933990090
• European Community (EC) Number: 811-157-7
• Nikkaji Number: J825.521K
• Mol file: 96163-72-3.mol

Synonyms:96163-72-3;(R)-Ethyl pyrrolidine-2-carboxylate;ethyl (2R)-pyrrolidine-2-carboxylate;d-proline ethyl ester;D-Proline, ethyl ester;D-proline-ethyl-ester;D-Proline,ethyl ester(9ci);SCHEMBL3330660;QPNJHVDIRZNKOX-ZCFIWIBFSA-N;(r)-2-ethyloxycarbonyl-pyrrolidine;(R)-Ethylpyrrolidine-2-carboxylate;WDA16372;MFCD17271681;AKOS017336928;D-Proline ethyl ester (H-D-Pro-OEt);AS-57807;CS-0080165;EN300-138280

Chemical Property of (R)-Ethyl pyrrolidine-2-carboxylate

Chemical Property:

• Refractive Index: 1.4480 to 1.4520
• Boiling Point: 191℃
• Flash Point: 70℃
• PSA: 38.33000
• Density: 1.031
• LogP: 0.63030
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Ethylpyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCCN1
• Isomeric SMILES: CCOC(=O)[C@H]1CCCN1

Technology Process of (R)-Ethyl pyrrolidine-2-carboxylate

There total 4 articles about (R)-Ethyl pyrrolidine-2-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: 89.4%

ethanol (64-17-5) + D-Prolin (344-25-2,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → ethyl proline hydrochloride (96163-72-3)

Guidance literature:

With thionyl chloride;

DOI:10.1007/BF00768332

Reference yield:

(+)-ethyl (3R,6S)-6-[(R)-1-phenylbutoxy]-1,2-oxazinane-3-carboxylate (575452-53-8) → ethyl proline hydrochloride (96163-72-3)

Guidance literature:

With hydrogen; boric acid; magnesium sulfate; nickel; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2004.11.009

Reference yield:

ethyl 3-bromo-2-(hydroxyimino)propanoate (73472-94-3) → ethyl proline hydrochloride (96163-72-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 48 percent / Na₂CO₃ / CH₂Cl₂ / 20 °C

2.1: NaCNBH₃ / acetic acid / 24 h / 0 - 20 °C

2.2: 63 percent / Et₃N / CHCl₃ / 8 h / Heating

3.1: H₂; H₃BO₃; MgSO₄ / Raney Ni / methanol / 48 h / 20 °C

With hydrogen; boric acid; sodium cyanoborohydride; sodium carbonate; magnesium sulfate; nickel; In methanol; dichloromethane; acetic acid;

DOI:10.1016/j.tet.2004.11.009

upstream raw materials:

ethanol

D-Prolin

(+)-ethyl (3R,6S)-6-[(R)-1-phenylbutoxy]-1,2-oxazinane-3-carboxylate

ethyl 3-bromo-2-(hydroxyimino)propanoate

Downstream raw materials:

(3S,8aR)-3-isobutyl-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

(3R,8aR)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

N-(tert-butyloxycarbonyl)-L-phenylalanyl-D-proline methyl ester

3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione

Refernces

• 1、 Schubert, Vivien,Di Meo, Florent,Saaidi, Pierre-Loic,Bartoschek, Stefan,Fiedler, Hans-Peter,Trouillas, Patrick,Suessmuth, Roderich D.. "Stereochemistry and conformation of skyllamycin, a non-ribosomally synthesized peptide from streptomyces sp. Acta 2897". . p. 4948 - 4955. Retrieved 2014/05/06.
• 2、 Nazarova, L. S.,Rozonov, Yu. B.,Likhosherstov, A. M.,Morozova, T. V.,Skoldinov, A. P.,et al.. "AZACYCLOALKANES. XXVII. SYNTHESIS AND ANTIANGINAL ACTIVITY OF NONACHLAZINE STEREOISOMERS". . p. 811 - 815. Retrieved 2007/10/02.