Ammonium Chloride → (2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydro-pyran-4-ol

Participants

Reaction Conditions

Reaction Steps

A solution of (1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (0.05 g, 0.19 mmol) in a 8:1 MeOH/H2O (2 ml) mixture was treated with NaN3 (0.061 g, 0.94 mmol) and NH4Cl (0.022 g, 0.41 mmol) and the resulting reaction mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ether and the organic layer was separated. Evaporation of the washed (saturated aqueous NaHCO3, water) ether extracts afforded a crude solid product. Purification of the product by flash chromatography (Hexane/Ethyl Acetate=4:1) yielded (2S,4R,5R)-5-Azido-2-benzhydryl-tetrahydropyran-4-ol 30a 0.05 g (95%, [α]D=(−)109.3, c=1, MeOH).

Provenance & Evidence