Acetic Acid → HCID 57678157, compound

Participants

Reaction Steps

To a stirred solution, 1 h, at 0° C. of 4-methylpiperidine (15.0 g, 151 mmol), 1-boc-4-piperidone (30.1 g, 151 mmol) and HOAc (18.2 g, 303 mmol) in THF (100 mL) was added sodium triacetoxyborohydride (64.2 g, 303 mmol) in 3 portions. The mixture was stirred at rt for 18 h. The reaction was neutralized with saturated K2CO3 and the pH was adjusted to 8 with saturated Na2CO3. The mixture was diluted with DCM and separated. The organic layer was washed with H2O and concentrated to provide the title compound of step A (33.0 g, 117 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ ppm 0.71-0.90 (m, 3H), 1.11-1.20 (m, 2H), 1.31-1.50 (m, 9H), 1.50-1.65 (m, 1H), 1.70-1.90 (m, 4H), 2.01-2.30 (m, 2H), 2.71-3.10 (m, 4H), 3.60-3.91 (m, 5H).

Provenance & Evidence