HCID 21103799, compound → (3R,5R)-5-((tert-Butyldimethylsilyl)oxy)piperidin-3-ol

Participants

Reaction Steps

A suspension of 329 (25.5 mmol) and 10% Pd/C (1 mol %) in MeOH (250 mL) was fitted with a balloon of hydrogen and allowed to stir at room temperature for 4 h. At that time, a vacuum was applied to remove any remaining hydrogen, the vessel was purged with nitrogen, diluted with MeOH (100 mL) and filtered through a pad of Celite on a fritted funnel. The resulting solution was concentrated to give 5-(R)-(tert-Butyl-dimethyl-silanyloxy)-piperidin-3-(R)-ol (330) as a colorless oil (25.0 mmol, 98% yield). 1H NMR (400 MHz, CD3OD) δ=0.13 ppm (s, 3H), 0.14 (s, 3H), 0.929 (s, 9H), 1.84 (br t, 2H, J=5 Hz), 2.71–2.78 (m, 2H), 2.97–3.05 (m, 2H), 4.04–4.09 (m, 1H), 4.19–4.24 (m, 1H).

Provenance & Evidence