Benzyl Alcohol → rel-1-(tert-butyl) 3-methyl (3R,5S)-5-aminopiperidine-1,3-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

(3R*,5S*)-1-(tert-Butoxycarbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid (575 mg) was suspended in toluene (10 ml), diphenylphosphoryl azide (0.52 ml) and triethylamine (0.34 ml) were added and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, benzyl alcohol (0.52 ml) and triethylamine (0.34 ml) were added and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was washed with water, 5% aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate and saturated brine in this order, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (1:4) was concentrated under reduced pressure. The obtained residue was dissolved in methanol (5 ml), 10% palladium-carbon (50% containing water) (70 mg) was added, and the mixture was subjected to catalytic reduction at ambient temperature under a hydrogen atmosphere (1 atm) for 12 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the object compound (370 mg) as an oil.

Provenance & Evidence