Acetic Acid → HCID 53392446, compound

Participants

Reaction Steps

A solution of 6-bromo-1-(pyrrolidin-3-yl)-1,2,3,4-tetrahydroquinoline (200 mg, 0.71 mmol) in 7 mL anhydrous methanol was treated with formaldehyde (37% aqueous solution, 79 μL, 1.07 mmol) followed by acetic acid (100 μL, 1.78 mmol). The solution was treated with sodium cyanoborohydride (67 mg, 1.07 mmol). The suspension was stirred at room temperature for 3 hours. The mixture was concentrated to dryness and partitioned between 20 mL 1N NaOH and 100 mL of CH2Cl2. After extraction, the organic layer was dried over Na2SO4, filtered and concentrated to give an oily residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (153 mg, 72.9%). 1H-NMR (CDCl3) δ 7.10 (dd, J=2.4, 8.7 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.57 (d, J=9.0 Hz, 1H), 4.47-4.38 (m, 1H), 3.26 (t, J=5.7 Hz, 2H), 2.81-2.68 (m, 4H), 2.60-2.55 (m, 1H), 2.40-2.24 (m, 1H), 2.35 (s, 3H), 2.24-2.13 (m, 1H), 1.92-1.79 (m, 3H). MS(ESI): 295.1 and 297.1 (M+1).

Provenance & Evidence