Acetic Acid → HCID 67444139, compound

Participants

Reaction Steps

To a suspension of the aldehyde 47 (0.3 g, 0.669 mmol) in a mixture of DCM (9 mL) and DMF (3 mL) were added 4-hydroxypiperidine (0.135 g, 1.34 mmol) and acetic acid (0.08 mL, 1.34 mmol) at RT. The reaction mixture was stirred for 30 min; NaBH(OAc)3 (0.425 g, 2.00 mmol) was added and the reaction mixture was stirred overnight. More 4-hydroxypiperidine (0.135 g, 1.34 mmol) and NaBH(OAc)3 (0.425 g, 2.00 mmol) were added to the reaction mixture that was stirred at room temperature for 4 hr, then quenched by addition of saturated NaHCO3 solution and extracted with DCM/MeOH. The organic layer was washed with brine and dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel (DCM/MeOH:90/10 to 75/25) then triturated with MeOH to afford title compound 599 (0.17 g, 48% yield) as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 8.71 (s, 1H), 8.56-8.53 (m, 1H), 8.52 (d, J=5.4 Hz, 1H), 8.31 (s, 1H), 8.23 (d, J=8.1 Hz, 1H), 7.85 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (dd, J=13.5, 2.4 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.24-7.18 (m, 1H), 6.65 (d, J=5.4 Hz, 1H), 6.56 (d, J=2.1 Hz, 1H), 4.58 (d, J=4.2 Hz, 1H), 3.54 (s, 2H), 3.50-3.40 (m, 1H), 2.75-2.65 (m, 2H), 2.60-2.50 (m, 1H), 2.19-2.05 (m, 2H), 1.80-1.65 (m, 2H), 1.50-1.35 (m, 2H), 0.71-0.64 (m, 2H), 0.48-0.40 (m, 2H).

Provenance & Evidence