949495-13-0

Upstream product

• 949495-12-9 (3S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-3-carboxylic acid 
• 765-30-0 Cyclopropylamine 
• 1373613-92-3 tert-butyl 3-{N-benzyloxycarbonyl-N-(ethoxycarbonylmethyl)amino}propionate 
• 1373613-93-4 3-{N-benzyloxycarbonyl-N-(ethoxycarbonylmethyl)amino}propionic acid 
• 501-53-1 benzyl chloroformate 
• 1373613-94-5 ethyl N-benzyloxycarbonyl-N-{(2-cyclopropylaminocarbonyl)ethyl}aminoacetate 
• 1373613-95-6 benzyl 3-(cyclopropylcarbamoyl)-4-oxopyrrolidine-1-carboxylate 
• 163116-18-5 N-ethoxycarbonylmethyl-β-alanine t-butyl ester 

Downstream Products

• 949495-14-1 benzyl (3S,4R)-3-((cyclopropylamino)methyl)-4-hydroxypyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

METHOD FOR PRODUCING 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE

The present invention provides an inexpensive and industrially advantageous method for producing an optically active form of an anti-(3S,4R)-3-alkylcarbamoyl-4-hydroxypyrrolidine derivative or it's enantiomer, which is a key intermediate for producing a high-quality optically active form of (3R,4S)-3-alkylaminomethyl-4-fluoropyrrolidine or it's enantiomer useful as an intermediate for producing pharmaceuticals. The present invention relates to a method for producing an optically active anti-(3S,4R)-4-hydroxypyrrolidine-3-carboxamide derivative, or it's enantiomer by carrying out asymmetric hydrogenation using an optically active catalyst of a 4-oxopyrrolidine-3-carboxamide derivative represented by the general formula (I). [in the formula (I), PG1 represents a protective group for an amino group, and R1 represents hydrogen, a C1 to C6 alkyl group which may be substituted, or a C3 to C8 cycloalkyl group which may be substituted].

PROCESS FOR PRODUCTION OF 3,4-DISUBSTITUTED PYRROLIDINE DERIVATIVE AND INTERMEDIATE FOR THE PRODUCTION

An industrially advantageous process for the production of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof that is useful as an intermediate for the production of novel antimicrobial agents 10-(3-cyclopropylaminomethyl-4-fluoropyrrolidinyl)pyridobenzox azine carboxylic acid derivatives. Highly stereoselective asymmetric hydrogenation of 1-protected-4-alkoxycarbonyl-3-oxopyrrolidine, followed by ester hydrolysis, followed by amidation with cyclopropylamine gives crude crystals. The crude crystals are purified by recrystallization to give a novel compound (3R,4S)-1-protected-3-cyclopropylcarbamoyl-4-hydroxypyrrolidin e or an enantiomer thereof at high optical purity. The use of these intermediates enables industrial production of high-quality products of (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine or an enantiomer thereof. The process is highly simple and can produce the desired products at high purity and stable yields.