Ammonium Chloride → 1-Boc-4-Methylenepiperidine

Participants

Reaction Conditions

Reaction Steps

1.6 g (14 mmol) potassium tert-butylate were added to a suspension of 5.34 g (15 mmol) methyltriphenylphosphonium bromide in 50 ml diethyl ether while stirring at 0° C. (ice bath). After stirring for 15 min, a solution of 2.00 g (10 mmol) 1-Boc-4-piperidone (A) in 15 ml diethyl ether was added slowly. The suspension was stirred for a further 30 min at 0° C. After the addition of 60 ml 10% aq. NH4Cl solution, the organic phase was separated off, dried over magnesium sulphate and desolventised under vacuum. After chromatography on silica gel (hexane:EtOAc=5:1), 1.71 g (89%) 4-methylene piperidine-1-carboxylic acid tert-butyl ester (B) were obtained as a colourless liquid.

Provenance & Evidence