3-(Piperidine-1-sulfonyl)benzoic acid → (3-(Piperidin-1-ylsulfonyl)phenyl)methanol

Participants

Reaction Steps

To a solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (538 mg, 2.00 mmol) in dry THF (8 mL) under nitrogen was added a solution of borane-THF complex in dry THF (1.0 M, 8 mL, 8.00 mmol) and the mixture then stirred for 18 hours at room temperature. The reaction was then quenched by the addition of excess methanol and evaporated in vacuo. The residue was partitioned between ethyl acetate and 2N HCl, and the separated organic layer washed successively with water and saturated brine, before being dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified using automated flash column chromatography on silica gel (gradient of 0 to 60% ethyl acetate in petrol) to afford (3-(piperidin-1-ylsulfonyl)phenyl)methanol (320 mg, 1.25 mmol, 63%).

Provenance & Evidence