Sodium borohydride → Tert-butyl 4-(hydroxy(pyridin-3-yl)methyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(1,1-dimethylethyloxycarbonyl)-4-(3-pyridinoyl)piperidine (5.0 g, 17.22 mmol) in methanol (75 mL) was cooled to 0° C. and sodium borohydride (1.30 g, 34.44 mmol) was added in four portions. The mixture was stirred at 0° C. for 1 h. The solvent was evaporated and the residue was partitioned between water (25 mL) and ethyl acetate (100 mL, 2×50 mL). The organic extracts were washed sequentially with 1N aqueous sodium hydroxide (25 mL) and brine (25 mL), combined, dried over Na2SO4, filtered and evaporated to afford the title alcohol as a white foam (5.02 g, 17.17 mmol, 99%). 1H NMR: δ8.45 (brs, 2H, H--C(2'), H--C(6')), 7.85 (brd, J=8.4 Hz, 1H, H--C(4')), 7.28 (dd, J=4.9, 8.4 Hz, 1H, H--C(5')), 4.43 (d, J=7.1 Hz, 1H, CHOH), 4.08 (m, 2H, eq-H--C(2)), 3.28 (exs, 1H, CHOH), 2.62 (m, 2H, ax-H--C(2)), 1.90 (m, 2H, eq-H--C(3)), 1.77 (m, 1H, H--C(4)), 1.43 (s, 9H, (CH3)3C), 1.28 (m, 2H, ax-H--C(3)). CIMS: m/z 293 (87%, (M+H)+ for C16H24N2O3), 265 (19), 237 (100), 219 (14), 175 (24).

Provenance & Evidence