Acetic Acid → HCID 86623332, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 1 (1 g, 6.793 mmol), N-tert-Butoxycarbonyl-4-piperidone (1.35 g, 6.793 mmol) and acetic acid (0.44 mL, 6.793 mmol) in 25 mL of 1,2-dichloroethane was cooled to 0° C. and treated with NaBH(OAc)3 (2.16 g, 10.19 mmol). The reaction was brought to room temperature and was stirred for 2 days. The solution was diluted with 3N NaOH solution (125 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4) and was concentrated. The crude product was subject to flash chromatography on silica gel using 5% ethyl acetate/hexanes. The sample was concentrated and dried resulting in a colourless viscous liquid, compound 2 (2.12 g, 94%). 1H NMR (CDCl3) δ 7.12-7.08 (m, 2H), 6.93 (d, J=7.8 Hz, 1H), 6.83 (t, J=14.7 Hz, 1H), 4.16-4.13 (m, 2H), 3.42 (tt, J=7.2, 22.2 Hz, 1H), 2.98 (brs, 2H), 2.85-2.75 (m, 4H), 1.88 (d, J=12.0 Hz, 2H), 1.73-1.60 (m, 6H), 1.47 (s, 9H); MS-ESI (m/z, %): 331 (MH+, 17), 275 (100).

Provenance & Evidence