171192-72-6

Basic information

• Product Name: (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate
• Synonyms: (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate
• CAS NO: 171192-72-6
• Molecular Weight: 249.31
• Mol File: 171192-72-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate(171192-72-6)
• EPA Substance Registry System: (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate(171192-72-6)

Safety Data

• Hazardous Substances Data: 171192-72-6(Hazardous Substances Data)

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 64-17-5 ethanol 
• 100-39-0 benzyl bromide 
• 2584-71-6 cis-hydroxy-D-proline 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 77449-99-1 (2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 100-44-7 benzyl chloride 
• 130930-27-7 (2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine 

Downstream Products

• 171192-74-8 (2R)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate 
• 169209-63-6 (2R,4R)-4-amino-4-carboxyproline 
• 171336-79-1 (2R,4S)-4-amino-4-carboxyproline 
• 174266-80-9 diethyl (2R,4R)-1-benzyl-4-aminopyrrolidine-2,4-dicarboxylate 
• 178963-35-4 (2R,4S)-4-Amino-1-benzyl-pyrrolidine-2,4-dicarboxylic acid diethyl ester 
• 174266-81-0 (2R,4R) diethyl-1-benzyl-4-(tert-butyloxycarbonylamino) pyrrolidine-2,4-dicarboxylate 
• 179030-55-8 (2R,4S)-1-Benzyl-4-tert-butoxycarbonylamino-pyrrolidine-2,4-dicarboxylic acid diethyl ester 
• 2584-71-6 cis-hydroxy-D-proline 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 635299-81-9 [(2R,4R)-1-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-pyrrolidin-2-yl]methanol 
• 627101-20-6 ethyl (2R,4R)-4-azido-1-benzylprolinate 
• 627101-18-2 ethyl (2R,4S)-1-benzyl-4-cyanoprolinate 
• 627101-22-8 (2R,4R)-(4-aminomethyl-1-benzylpyrrolidin-2-yl)methanol 

Relevant articles and documents

A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines

A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2S,4S)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity.

MODULATORS OF CELLULAR ADHESION

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

Ex-chiral pool synthesis and receptor binding studies of 4-substituted prolinol derivatives

Starting from natural 4-hydroxyproline, preparation of the four possible stereoisomers of 4-amino- and 4-aminomethyl-substituted prolinol derivatives, respectively, was accomplished by chemo- and regioselective functional group transformations at the 2- and 4-positions of the pyrrolidine moiety. These building blocks were used as valuable precursors for the preparation of new methoxybenzamide derivatives. Dopamine and serotonin binding studies involving the subtypes D1, D2long, D2short, D3 and D4 as well as 5-HT1A and 5-HT2, respectively, displayed interesting structure activity relationships, especially with respect to the absolute and relative configuration of the test compounds. As a complement to the D3 receptor preferring aminomethylpyrrolidine FAUC 21, the (2R,4R)-aminoprolinol derivative ent-24 (FAUC 65) preferentially recognizing the D4 subtype was developed.