Borane → Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1M solution of borane in THF (15.8 ml, 15.8 mmol) was added slowly to a solution of 2-(1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)acetic acid (40) (1.02 g, 3.94 mmol) at 0° C. After stirring the mixture at 0° C. for 1 hour and at rt for 16 hours the reaction was quenched by addition of NH4Cl solution and extracted with ethyl acetate. The organic layer was then washed with water and brine, dried over Na2 SO4 and evaporated. The crude product was purified by flash chromatography (silica gel, EtOAc/n-pentane) which furnished the product as colorless oil.

Provenance & Evidence