Dimethyl Sulfide → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

Participants

Reaction Steps

A suspension of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.750 g, 3.08 mmol) in THF (5 mL) at rt under N2 was treated with 2M THF solution of BH3 SMe2 (1.541 mL, 3.08 mmol). After 18 h, the reaction was cooled in an ice bath and quenched by the addition of 5 mL of 1N NaOH. Partitioned between ether and water. Organic phase dried (MgSO4), filtered, and concentrated in vacuo to give 700 mg (99%) of tert-butyl 4-(hydroxymethyl)-4-methylpiperidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 3.86-3.64 (m, 3H), 3.41 (s, 2H), 3.15 (ddd, J=13.6, 10.2, 3.5 Hz, 2H), 1.94-1.80 (m, 1H), 1.52-1.43 (m, 10H), 1.31 (dt, J=13.5, 3.8 Hz, 2H), 1.01 (s, 3H).

Provenance & Evidence