Sodium Hydroxide → (RS)-1-[(3SR,4SR)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol

Participants

Reaction Conditions

Reaction Steps

Under an inert atmosphere a 100 mL four necked flask (flame dried) with a magnetic stirrer was charged with 835 mg (2.54 mmol) 1-[(3SR,4SR)-1-benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanone in 25 mL THF. The yellow solution was cooled to 0° C. and 34 mg (0.89 mmol) LiAlH4 was added. The mixture was stirred for 30 min at 0° C. and 30 min from 0° C. to 15° C. At 0° C. 10 mL ethyl acetate was added drop-wise, followed by 5 mL THF:water 9:1 and 1 mL 4 N aqueous NaOH and 1 mL water. The mixture was stirred for 30 min at 40-50° C. and Na2SO4 was added. The mixture was filtered off and concentrated under vacuum. The residue was purified by chromatography on silica eluting with a gradient formed from DCM, methanol, NH3aq. to yield after evaporation of the product containing fractions 466 mg (55%) of the title compound as off-white foam. MS (m/e): 330.1 [(M+H)+].

Provenance & Evidence