Methanol → HCID 86700542, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-5-methyl-6-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (10 g, 35 mmol) in THF (150 mL) was added borane dimethylsulfide complex (49 mL, 49 mmol). The reaction mixture was stirred at 0° C. for 1 h, and then stirred at 40° C. for 3 h. Methanol was added and the reaction mixture was concentrated, washed with 1 M HCl, and extracted with EtOAc/water to give the oil layer, which was dried, and concentrated. The crude product was purified by silica gel chromatography (20:1 petroleum ether:EtOAc) to provide the title intermediate (2 g, 21% yield). (m/z): [M−100+H]+ calcd for C14H25NO4 172.18 found 172.2.

Provenance & Evidence