Triacetoxyperiodinane → HCID 68171040, compound

Participants

Reaction Steps

To a solution of (1R,2S)-ethyl 1-(bis(tert-butoxycarbonyl)amino)-2-(2-hydroxyhex-5-enyl)cyclopropanecarboxylate (4.3 g, 10 mmol) in dichloromethane (50 ml) at 25° C. was added Dess-Martin Periodinane (5.97 g, 14.1 mmol). The reaction mixture was stirred for 3 h and quenched with 1 N aqueous sodium thiosulfate solution (50 mL) and saturated aqueous sodium bicarbonate solution (15 mL), and the reaction mixture stirred for 1 h. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced. The crude product was purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide (1R,2S)-ethyl 1-(bis(tert-butoxycarbonyl)amino)-2-(2-oxohex-5-enyl)cyclopropane carboxylate (3.8 g, 88% yield) as an oil. MS (ESI): m/z=448.1 [M+Na].

Provenance & Evidence