L-Proline, 4-hydroxy-1-(phenylmethyl)-, ethyl ester, (4R)-

Base Information

• Chemical Name: L-Proline, 4-hydroxy-1-(phenylmethyl)-, ethyl ester, (4R)-
• CAS No.: 154342-88-8
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Mol file: 154342-88-8.mol

Synonyms:

Chemical Property of L-Proline, 4-hydroxy-1-(phenylmethyl)-, ethyl ester, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Proline, 4-hydroxy-1-(phenylmethyl)-, ethyl ester, (4R)-

There total 6 articles about L-Proline, 4-hydroxy-1-(phenylmethyl)-, ethyl ester, (4R)- 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: 80.0%

benzyl bromide (100-39-0) + (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester (61478-25-9) → (2S,4R)-ethyl N1-benzyl-4-hydroxypyrrolidine-2-carboxylate (154342-88-8)

Guidance literature:

benzyl bromide; (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester; With triethylamine; In dichloromethane; at 20 ℃; for 12h; Heating / reflux;

With sodium hydroxide; water; In dichloromethane;

Reference yield: 70.0%

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) + benzyl chloride (100-44-7) → (2S,4R)-ethyl N1-benzyl-4-hydroxypyrrolidine-2-carboxylate (154342-88-8)

Guidance literature:

With triethylamine; In dichloromethane; for 6h; Heating;

DOI:10.1016/0957-4166(95)00209-8

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) + benzyl bromide (100-39-0) → (2S,4R)-ethyl N1-benzyl-4-hydroxypyrrolidine-2-carboxylate (154342-88-8)

Guidance literature:

trans-4-hydroxy-L-proline ethyl ester hydrochloride; benzyl bromide; With triethylamine; In chloroform; for 6h; Heating;

With sodium hydroxide; In chloroform; at 20 ℃;

DOI:10.1016/j.tetasy.2003.08.019

upstream raw materials:

trans-4-hydroxy-L-proline ethyl ester hydrochloride

benzyl chloride

benzyl bromide

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester

Downstream raw materials:

(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

(2S,4S)-1-benzyl-2-ethoxycarbonylpyrrolidine-4-spiro-5'-hydantoin

(2S,4S)-1-Benzyl-4-tert-butoxycarbonylamino-pyrrolidine-2,4-dicarboxylic acid diethyl ester

(2S,4R)-1-Benzyl-4-tert-butoxycarbonylamino-pyrrolidine-2,4-dicarboxylic acid diethyl ester

Refernces

• 1、 Schann, Stephan,Menet, Christel,Arvault, Paul,Mercier, Geraldine,Frauli, Melanie,Mayer, Stanislas,Hubert, Nadia,Triballeau, Nicolas,Bertrand, Hugues-Olivier,Acher, Francine,Neuville, Pascal. "Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist". . p. 4856 - 4860. Retrieved 2007/10/03.
• 2、 Heindl, Cornelia,Huebner, Harald,Gmeiner, Peter. "Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives". . p. 3141 - 3152. Retrieved 2007/10/03.