Acetic Acid → HCID 67443204, compound

Participants

Reaction Steps

3,3-Difluoropiperidine hydrochloride (0.250 g, 2.06 mmol) was suspended in DCM and washed with 3M NaOH. The organic phase was separated, dried over anhydrous MgSO4 and filtered into a solution of aldehyde 47 (0.100 g, 0.22 mmol) and acetic acid (0.04 mL, 0.7 mmol) in a 10:1 dichloromethane/DMF mixture (45 mL) which was stirred for 20 min at RT. Then sodium triacetoxyborohydride (0.142 g, 0.67 mmol) was added and the reaction mixture was stirred at RT for 18 h and partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous NaHCO3, then dried (anhydrous MgSO4) and concentrated. Silica gel chromatography of the residue (10% methanol/chloroform) afforded title compound 316 (0.055 g, 45% yield) as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.72 (s, 1H); 8.56 (d, J=2.7, 1H); 8.52 (d, J=5.3, 1H); 8.32 (s, 1H); 8.23 (d, J=8.0, 1H); 7.88 (d, J=8.2, 1H); 7.73 (dd, J=13.7, 1H); 7.38 (t, J=9.0, 1H); 7.22-7.18 (m, 1H); 6.65 (d, J=5.3, 1H); 6.60 (s, 1H); 3.62 (s, 2H); 135-3.30 (m, 4H?, under water peak); 2.57-2.52 (m, 1H); 2.00-1.90 (m 2H); 0.67-0.63 (m, 2H); 0.45-0.41 (m, 2H). MS (m/z): 554.6 (M+1).

Provenance & Evidence