159830-01-0

Basic information

• Product Name: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
• Synonyms: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
• CAS NO: 159830-01-0
• Molecular Weight: 317.385
• Mol File: 159830-01-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester(159830-01-0)
• EPA Substance Registry System: (S)-4-methylene-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester(159830-01-0)

Safety Data

• Hazardous Substances Data: 159830-01-0(Hazardous Substances Data)

Upstream product

• 163190-46-3 tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-39-0 benzyl bromide 
• 84348-38-9 (S)-1-(tert-butoxycarbonyl)-4-methylenepyrrolidine-2-carboxylic acid 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 

Downstream Products

• 20309-87-9 (2S)-4-methylenepyrrolidine-2-carboxylic acid 

Relevant articles and documents

An enantioselective approach to 4-substituted proline scaffolds: Synthesis of (s)-5-(tert-butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid

A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir.

PYRROLIDINE DERIVATIVES AND THEIR USE AS COMPLEMENT PATHWAY MODULATORS

The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses as complement alternative inhibitors for the treatment of ocular diseases. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

A Short and Efficient Synthesis of (S)-4-Methylene Proline Benzyl Ester from (S)-Pyroglutamic Acid

(S)-4-methylene proline benzyl ester 2 was synthesized from benzyl N-tert-butoxycarbonyl pyroglutamate through a Mannich and a Cope elimination reactions.