Pyridine → 1,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamate

Participants

Reaction Steps

To a solution of pyridine--sulfur trioxide complex (5.1 g, 32 mmol) in dimethyl sulfoxide (20 ml)--dichloromethane (20 ml) was added dropwise a solution of (S)-N-(tert-butoxycarbonyl)-isoleucinol (1.4 g, 6.5 mmol) and triethylamine (3.2 g, 32 mmol) in dimethyl sulfoxide (20 ml)--dichloromethane (20 ml) under an argon gas stream and ice-cooling. After stirring for 30 minutes, the reaction solution was poured into water, and extracted with dichloromethane. The organic layer was washed with a saturated aqueous citric acid solution, an aqueous sodium bicarbonate solution, water and an aqueous sodium chloride solution, successively. After drying over sodium sulfate, the solvent was evaporated under reduced pressure to give (2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanal (1.3 g).

Provenance & Evidence