Hydrogen Peroxide → HCID 97107398, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring mixture of NaBH4 (0.93 g, 24.6 mmol) in THF (25 mL) cooled to 0° C. was added boron trifluoride etherate (3.2 mL, 25 mmol) and the mixture was allowed to warm up to rt over 1 h. It was then re-cooled to 0° C. and to it was added a solution of tert-butyl 4-(4-(benzyloxy)-phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (3 g, 8.2 mmol) in THF (10 mL). The resulting mixture was allowed to warm up to rt over 2 h. The reaction mixture was cooled again to 0° C. and H2O (10 mL), ethanol (10 mL), 10 M NaOH (10 mL) and H2O2 (8 mL, 26 mmol) were sequentially added. The final mixture was heated to 65° C. overnight. After cooling, the reaction was quenched with water and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo yielding 2.7 g of (±)-rel-(3S,4S)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (82% yield) as off-white solid. LCMS (method O) RT 2.41 min, m/z 382 (M−H). 1H NMR (400 MHz, DMSO-d6) δ 1.41 (s, 9H), 1.63 (m, 1H), 1.67 (m, 1H), 2.67 (m, 1H), 3.37-3.41 (m, 1H), 3.92 (m, 1H), 4.10 (m, 1H), 4.73 (d, J=2.4, 1H), 5.07 (s, 2H), 6.91 (d, J=9, 2H), 7.14 (d, J=9, 2H), 7.31-7.44 (m, 4H).

Provenance & Evidence