178755-15-2

Upstream product

• 100-46-9 benzylamine 
• 178755-13-0 (2S,3R)-2-(tert-Butoxycarbonyl)amino-1,4-bis(methanesulfonyloxy)-3-ethylbutane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 181216-51-3 (2S,3R)-2-Amino-3-ethylbutane-1,4-diol 
• 181216-52-4 (2S,3R)-2-(tert-Butoxycarbonyl)amino-3-ethylbutane-1,4-diol 
• 181216-50-2 (2S,3R)-2-[N-Benzyl-N-(9-phenylfluoren-9-yl)]amino-3-ethylbutane-1,4-diol 

Relevant academic research and scientific papers

Process for preparation of chiral 3-amino-pyrrolidine and analogous bicyclic compounds

A process for the preparation of chiral 3-aminopyrrolidine and analogous bicyclic derivatives from dihydroxy olefins by treatment with titanium isopropoxide, an optically active tartrate ester and tert-butyl hydroperoxide, followed by subsequent alkylatio

A large-scale preparation of (3S,4S)-3-(tert-butoxycarbonyl)amino-4-methylpyrrolidine and its analogs from L-aspartic acid

(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (12a) was synthesized from L-aspartic acid (4) on a large scale. Methylation of dimethyl (2S)-N-benzyl-N-(9-phenylfluoren-9-yl)aspartate (5), easily derived from 4, with methyl iodide gave (3R)-3-methylaspartate (6a) in 91% yield with high diastereoselectivity. Reduction of 6a with lithium aluminum hydride, followed by hydrogenolysis, protection with di-tert-butyl dicarbonate, and mesylation gave 10a in 89% overall yield. Subsequently, reaction of 10a with benzylamine under a nitrogen atmosphere at room temperature, followed by hydrogenolysis, gave the target compound (12a) in 65% overall yield. In a similar manner to that described for the preparation of 12a from 5, compound 5 was converted into 4-ethyl and 4-propyl derivatives (12b,c) in 34% and 38% overall yields.