Sodium Hydroxide → 1-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanone

Participants

Reaction Steps

To a solution of piperidin-3-ylmethanol (10 g, 86.83 mmol) in water (25 mL), was added a solution of NaOH (13.89 g, 347.31 mmol) in water (25 mL) dropwise at 0° C. The mixture was stirred for 15 minutes, after which time, a solution of 3-methylbutanoyl chloride (20.94 g, 173.66 mmol) in THF (25 mL) was added dropwise with vigorous stirring. The reaction was slowly warmed to room temperature and, upon completion was diluted with Et2O (500 mL) was added with vigorous stirring. After 15 minutes, the phases were separated, and the aqueous phase was extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over Na2SO4, concentrated under reduced pressure and flash chromatographed on silica gel (0-100% EtOAc in hexanes) to give the title compound as a colorless oil (16.27 g, 94%). MS 200 (MH+).

Provenance & Evidence