N-Benzyl-L-proline ethyl ester

Base Information

• Chemical Name: N-Benzyl-L-proline ethyl ester
• CAS No.: 955-40-8
• Molecular Formula: C14H19 N O2
• Molecular Weight: 233.31
• Hs Code.: 2933990090
• European Community (EC) Number: 627-933-1
• DSSTox Substance ID: DTXSID40350814
• Nikkaji Number: J725.669H
• Wikidata: Q82126916
• Mol file: 955-40-8.mol

Synonyms:955-40-8;N-Benzyl-L-proline ethyl ester;(S)-Ethyl 1-benzylpyrrolidine-2-carboxylate;ethyl (2S)-1-benzylpyrrolidine-2-carboxylate;ethyl benzyl-L-prolinate;Ethyl 1-benzyl-L-prolinate;ethyl 1-benzylprolinate;N-benzyl-proline ethyl ester;SCHEMBL1188654;DTXSID40350814;FLASAKCDOWUBQX-ZDUSSCGKSA-N;Ethyl 1-(phenylmethyl)-L-prolinate;MFCD00075531;AKOS016843123;AT38558;N-Benzyl-L-proline ethyl ester, 97%;CS-0159375;EN300-731653

Chemical Property of N-Benzyl-L-proline ethyl ester

Chemical Property:

• Vapor Pressure: 0.15 mm Hg ( 100 °C)
• Refractive Index: n20/D 1.511(lit.)
• Boiling Point: 308.9oC at 760 mmHg
• Flash Point: >230 °F
• PSA: 29.54000
• Density: 1.048 g/mL at 25oC(lit.)
• LogP: 2.15200
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 233.141578849
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

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

N-Benzyl-L-proline ethyl ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1CCCN1CC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@@H]1CCCN1CC2=CC=CC=C2

Technology Process of N-Benzyl-L-proline ethyl ester

There total 5 articles about N-Benzyl-L-proline ethyl ester 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: 44.0%

methanol (67-56-1) + dimethyl 2-{[N2-(1-benzylpyrrolidin-2-yl)carbonyl]hydrazino}-3-cyanobut-2-enedioate → dimethyl 3-amino-1H-pyrazole-4,5-dicarboxylate + N-benzyl-L-proline ethyl ester (955-40-8,172478-10-3)

Guidance literature:

In methanol; at 20 ℃;

DOI:10.3987/COM-12-S(N)16

Reference yield:

benzyl bromide (100-39-0) + ethyl (2S)-pyrrolidine-2-carboxylate (5817-26-5) → N-benzyl-L-proline ethyl ester (955-40-8,172478-10-3)

Guidance literature:

With potassium carbonate; In acetone; at 25 ℃; for 12h;

DOI:10.1021/ol401425s

Reference yield:

ethanol (64-17-5) + N-benzyl-L-proline (31795-93-4) → N-benzyl-L-proline ethyl ester (955-40-8,172478-10-3)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.tetasy.2012.05.010

upstream raw materials:

O-benzyl-N,N'-dicyclohexylisourea

ethyl (2S)-pyrrolidine-2-carboxylate

L-proline

ethanol

Downstream raw materials:

(S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine

ethyl 2-(2-nitroethyl)-1-benzylpyrrolidine-2-carboxylate

1-((S)-1-benzyl-pyrrolidin-2-yl)-cyclopropanol

(2S)-1-benzyl-N'-[(E)-(4-methoxyphenyl)methylidene]pyrrolidine-2-carbohydrazide

Refernces

• 1、 Mloston, Grzegorz,Pieczonka, Adam M.,Wroblewska, Aneta,Linden, Anthony,Heimgartner, Heinz. "Studies on the synthesis and some reactions of (S)-proline hydrazides". experimental part. p. 795 - 801. Retrieved 2012/09/07.
• 2、 Enders, Dieter,Kipphardt, Helmut,Gerdes, Peter,Brena-Valle, Leonardo J.,Bhushan, Vidya. "LARGE SCALE PREPARATION OF VERSATILE CHIRAL AUXILIARIES DERIVED FROM (S)-PROLINE". . p. 691 - 704. Retrieved 2007/10/02.