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

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (0.95 g, 25 mmol) was added to a solution of 1-Boc-4-piperidone (2.50 g, 12.5 mmol) in MeOH (25 mL) at 0° C. The resulting mixture was stirred at 0° C. for 2 hours, then room temperature for 2 hours. The mixture was diluted with water (100 mL) and brine (100 mL) then extracted with EtOAc (2×150 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound A110 as a thick colorless oil (2.47 g, 98%); 1H NMR (400 MHz, CDCl3) δ 3.91-3.79 (m, 3H), 3.02 (m, 2H), 1.93-1.78 (m, 2H), 1.56 (d, J=4.2 Hz, 1H), 1.52-1.40 (m, 11H).

Provenance & Evidence