tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

A mixture of N-(tert-butoxycarbonyl)-piperidin-4-one (4.90 g, 24.59 mmol), sodium borohydride (1.52 g, 40.18 mmol) and methanol was stirred for 10 h. The solvent was removed by rotary evaporation. The residue was treated with portions of acetone (4×20 mL) and evaporated each time on a rotary evaporator. Water (10 mL) was added and the product was extracted with CHCl3 (4×20 mL). The combined CHCl3 extracts were dried (K2CO3), filtered and concentrated to afford 3.80 g (76.8%) of a thick syrup, that solidified upon standing.

Provenance & Evidence