143878-86-8

Basic information

• Product Name: (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester
• Synonyms: (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester
• CAS NO: 143878-86-8
• Molecular Weight: 247.337
• Mol File: 143878-86-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester(143878-86-8)
• EPA Substance Registry System: (2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester(143878-86-8)

Safety Data

• Hazardous Substances Data: 143878-86-8(Hazardous Substances Data)

Upstream product

• 38806-09-6 1-acetylcyclopropanecarboxylic acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 
• 143878-85-7 1-(1(S)-phenylethyl)-2-methyl-4,5-dihydropyrrole-3-carboxylic acid methyl ester 
• 56553-60-7 sodium tris(acetoxy)borohydride 
• 143955-12-8 methyl 2-acetylcyclopropanecarboxylate 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 664364-31-2 2-[(2S,3S)-2-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-yl]propane-2-ol 
• 664364-34-5 (2S,3S)-1-[(tert-butoxy)carbonyl]-2-methylpyrrolidine-3-carboxylic acid 
• 1004750-59-7 methyl (2S,3R)-2-methyl-1-[(S)-1-phenylethyl]pyrrolidine-3-carboxylate 
• 143878-87-9 methyl (2S,3S)-2-methylpyrrolidine-3-carboxylate 

Relevant articles and documents

NOVEL COMPOUNDS

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

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.

Enamino ester reduction: A short enantioselective route to pyrrolizidine and indolizidine alkaloids. Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol

Various chiral pyrrolidine tetrasubstituted β-enamino esters were reduced catalytically or chemically with good to moderate diastereoselectivity owing to a chiral induction originated from (S)-α- methylbenzylamine. With endocyclic double bond compounds, t