Triacetoxyperiodinane → HCID 86596966, compound

Participants

Reaction Steps

The compound benzyl (1S,2R,4R)-2-((tert-butyldimethylsilyloxy)methyl)-4-hydroxycyclohexylcarbamate (4.15 g) in CH2Cl2 (30 mL) was added to Dess-Martin periodane (13.4 g, 31.6 mmol) in CH2Cl2 (100 mL) at 0° C. After 1 h, the ice bath was removed and the reaction aws stirred overnight. This mixture was diluted with ether (425 mL) and washed with water (2×50 mL), sat'd Na2S2O3 (2×50 mL), 1N sodium hydroxide (2×50 mL), and brine (1×50 mL). The organic layer was dried over MgSO4, filtered, and then evaporated to dryness to give benzyl (1S,2R)-2-((tert-butyldimethylsilyloxy)methyl)-4-oxocyclohexylcarbamate (4.05 g) as a clear viscous oil after drying under vacuum overnight. MS found: (M+H)+=392.

Provenance & Evidence