1004750-59-7

Basic information

• Product Name: methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate
• Synonyms: methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate
• CAS NO: 1004750-59-7
• Molecular Weight: 247.337
• Mol File: 1004750-59-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate(1004750-59-7)
• EPA Substance Registry System: methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate(1004750-59-7)

Safety Data

• Hazardous Substances Data: 1004750-59-7(Hazardous Substances Data)

Upstream product

• 143878-86-8 (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester 

Relevant articles and documents

Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol

The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with α-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with α-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the β-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.