Borane;tetrahydrofuran → tert-Butyl 4-(hydroxymethyl)-4-(pyridin-3-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 1-(tert-butoxycarbonyl)-4-(pyridin-3-yl)piperidine-4-carboxylic acid (4.0 g, 13.06 mmol) and tetrahydrofuran (25 mL). The reaction was placed under N2. To the flask was added Borane/THF (26.1 mL of 1M soln, 26.1 mmol) and set to reflux for 2 hours. The reaction was cooled to 0° C. and quenched with MeOH (100 mL). The solution was then conc. in vacuo. The residue was purified via column chromatography (5% MeOH/95% CH2Cl2) to yield 3.2 g (84%). Mass Spec.: 293.26 (MH)+. LC: tr=1.65 min HPLC Method 1. 1H-NMR (CD3OD, 400 MHz) δ 8.56 (s, 1H), 8.45 (d, 1H), 8.10 (d, 1H), 7.59 (m, 1H), 3.67 (m, 2H), 3.56 (s, 2H), 3.11 (t, 2H), 2.11 (d, 2H), 1.85 (m, 2H), 1.43 (s, 9H).

Provenance & Evidence