(Dimethyl sulfide)trihydroboron → Tert-butyl 3-cyclohexyl-3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-(tert-butoxycarbonyl)-3-cyclohexyl-8-azabicyclo[3.2.1]octane-3-carboxylic acid (3-2) (1.47 g, 4.35 mmol) in 50 mL of anhydrous tetrahydrofuran was added borane-methyl sulfide complex (8.70 mL, 17.4 mmol, 2.0 M in tetrahydrofuran) dropwise at room temperature. The mixture was stirred at 50° C. for 48 hours and the volatiles were removed under vacuum Purification of the crude residue by flash chromatography over silica gel (50% ethyl acetate/hexanes as eluent) afforded (3-3) as a white solid.

Provenance & Evidence