Acetone → HCID 178440170, compound

Participants

Reaction Steps

A solution of 5-cyano-4-[2-(1-oxo-2,2,2-trifluoroethyl)-1H-pyrrol-1-yl]-2 propyl-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole (Example 27, 300 mg) in ethanol (5 mL) was chilled to 10° C. and treated with NaBH4 (30 mg). There was a period of rapid gas evolution then the reaction was stirred for 1 hour. Acetone (0.1 mL) was added and the reaction was stirred 10 minutes longer before partitioning between ethyl acetate and 10% citric acid (aq). The organic layer was washed with saturated aqueous NaCl, dried over MgSO4 and evaporated. Flash chromatography on silica gel, eluting with CHCl3CH3OH--CH3CN (90:5:5) gives the title compound as a foam upon evaporation of solvents. The foam was triturated with hexane diisopropyl ether (3:1) to give a colorless powder. MS (FAB, thioglycerol) 533 (m+1).

Provenance & Evidence