Borane → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a 0° C. solution of 15.0 g (65.5 mmole) of the 4-carboxy-piperidine-1-carboxylic acid-t-butyl ester produced above, in 200 ml of dry tetrahydrofuran, under nitrogen gas, was added 98.2 ml (98.2 mmole) of 1.0 M borane in tetrahydrofuran over 10 minutes. The reaction mixture was stirred an additional 4 hours at room temperature, quenched with 500 ml of aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to give 14.1 g of 4-hydroxymethyl-piperidine-1-carboxylic acid t-butyl ester as a white solid with melting point 75°-76° C.

Provenance & Evidence