1-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid → HCID 66811101, compound

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (416 mg, 1.36 mmol) in THF (2 ml) at 0° C. was added 1M borane-THF complex in THF (4.1 ml, 3.01 mmol). The reaction was warmed to rt and allowed to stir for 18 h. The reaction was cooled to 0° C., quenched with the careful addition of methanol, and concentrated in vacuo to yield tert-butyl 2-(hydroxymethyl)-3-phenylpiperidine-1-carboxylate (82%). HRMS (ES, M+Na) calcd for C17H25NO3: 314.1726, found: 314.1720. 1H NMR (400 MHz, CD3OD) δ 7.34-7.13 (m, 5H), 4.46 (m, 1H), 4.06 (d, J=13.0 Hz, 1H), 3.75 (m, 1H), 3.09 (m, 1.5H), 2.99 (m, 1.5H), 2.06 (m, 1H), 1.82 (m, 2H), 1.59 (m, 1H), 1.48 (s, 9H).

Provenance & Evidence