143771-06-6

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-(2-hydroxyethyl)-, phenylmethyl ester, (S)-
• CAS NO: 143771-06-6
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Mol File: 143771-06-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-(2-hydroxyethyl)-, phenylmethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-(2-hydroxyethyl)-, phenylmethyl ester, (S)-(143771-06-6)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-(2-hydroxyethyl)-, phenylmethyl ester, (S)-(143771-06-6)

Safety Data

• Hazardous Substances Data: 143771-06-6(Hazardous Substances Data)

Upstream product

• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 6216-63-3 N-Cbz-Prolinol 
• 1446128-16-0 benzyl (2S)-2-[(E)-2-nitrovinyl]pyrrolidine-1-carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 147-85-3 L-proline 
• 1000806-50-7 (E)-(6-benzyloxycarbonylamino)-2-hexenal 
• 67036-44-6 methyl (S)-2-(5-oxopyrrolidin-2-yl)acetate 
• 56633-72-8 (-)-(S)-2-methoxycarbonylmethylpyrrolidine-1-carboxylic acid benzyl ester 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 56633-71-7 2-(S)-(2-diazo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 56633-73-9 (S)-2-(1-((benzyloxy)carbonyl)pyrrolidine-2-yl)acetic acid 
• 501-53-1 benzyl chloroformate 
• 149427-84-9 (S)-5-(2-hydroxy-ethyl)-pyrrolidin-2-one 

Downstream Products

• 18881-13-5 (+)-coniceine 
• 1226904-85-3 (S)-2-(2-iodoethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 143771-08-8 (S)-2-((E)-4-Oxo-hept-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 143771-09-9 (R)-2-(4-Oxo-heptyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 191528-62-8 (2-Azido-phenyl)-[(S)-2-(2-hydroxy-ethyl)-pyrrolidin-1-yl]-methanone 
• 191528-63-9 [(S)-1-(2-Azido-benzoyl)-pyrrolidin-2-yl]-acetaldehyde 
• 152141-40-7 (S)-hexahydroindolizin-5(1H)-one 

Relevant articles and documents

The synthesis of a novel benzodiazocine via an intramolecular Staudinger/aza-Wittig cyclization

The novel pyrrolobenzodiazocine (1) has been prepared by an intramolecular Staudinger/aza Wittig protocol from the precursor azido aldehyde (2) in a remarkable 93% yield. Aldehyde (2) was prepared by coupling protected homoprolinol with 2-azidobenzoic aci

Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate

The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement.

Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis

N-Z-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described.