Sodium borohydride → HCID 86586719, compound

Participants

Reaction Steps

A mixture of (1R*,2R*,5S*,6R*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-phenylthiomethyl-1,2,3-triazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane and (1R*,2R*,5S*,6R*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(3-phenylthiomethyl-1,2,3-triazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 100; 99 mg, 0.1 mmol) and nickel(II)chloride hexahydrate (233 mg, 1.0 mmol) in methanol (6 ml) and THF (2 ml) at 0° C. was treated with sodium borohydride (112 mg, 2.9 mmol). A black precipitate was formed and the mixture was stirred for 20 minutes. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The isomers were separated by preparative TLC eluting with 1:1 ethyl acetate/hexane to afford the title compounds (3-methyl-1,2,3-triazol-5-yl isomer: 17 mg) and (1-methyl-1,2,3-triazol-5-yl isomer: 34 mg), in a combined yield of 61%.

Provenance & Evidence