Acetic Acid → HCID 131724529, compound

Participants

Reaction Steps

To a solution of (±)-trans-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline from EXAMPLE 4 (95 mg, 0.44 mmol) in 5 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.043 mL, 0.53 mmol), sodium triacetoxyborohydride (168 mg, 0.79 mmol) and glacial acetic acid (0.027 mL, 0.48 mmol). The resulting mixture was stirred at ambient temperature for 1 h and then the reaction was quenched with water. The mixture was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. The residue was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (0.44 mL, 0.88 mmol). A solid precipitated out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford 35 mg (27%) of the title compound of EXAMPLE 6 as an off white powder. 1H NMR (d6-dmso): δ 11.22 (broad s, 1H), 6.76 (d, 1H, J=7.7 Hz), 6.57 (dd, 1H, J=7.3, 12.5 Hz), 6.38 (t, 1H, J=7.3 Hz), 4.17-4.08 (m, 1H), 3.81-3.72 (m, 1H), 3.68-3.60 (m, 1H), 3.42-3.18 (m, 5H), 2.98-2.80 (m, 4H), 2.66-2.60 (m, 2H), 2.10-1.98 (m, 1H), 1.95-1.83 (m, 1H), 1.82-1.72 (m, 1H). LRMS (ES)+: 229.4 (M+H)+.

Provenance & Evidence