Water → 1-Benzyl-4-isopropylpiperidin-4-ol

Participants

Reaction Steps

Under a nitrogen atmosphere, first 700 mL of a THF/diethyl ether mixture (2:1) and then a solution of 53.0 mL (283 mmol) of N-benzyl-4-piperidone in 200 mL of a THF/diethyl ether mixture (2:1) were slowly added at −15° C. to 200 mL (400 mmol, 2 M in THF) of isopropylmagnesium chloride solution and the reaction mixture was stirred for 1 hour between −3° C. and −6° C. While cooling with ice, 600 mL of water was slowly added dropwise and the mixture was stirred for 30 minutes. Then 400 mL of EtOAc and 100 mL of diethyl ether were added. The organic phase was separated off and dried over sodium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography (silica gel, DCM/MeOH/NH3 98:2:0.2). Yield: 9.85 g (15% of theoretical); C15H23NO (M=233.349); calc.: molpeak (M+H)+: 234; found: molpeak (M+H)+: 234; HPLC-MS: 4.1 minutes (method G).

Provenance & Evidence