Hydrochloric Acid → HCID 131724528, compound

Participants

Reaction Steps

To a solution of (±)-trans-5,6,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinolin-8(8aH)-one, hydrochloride salt from EXAMPLE 3 (200 mg, 0.76 mmol) in 5 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.065 mL, 0.76 mmol) and sodium triacetoxyborohydride (260 mg, 1.22 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. A portion of the residue (50 mg, 0.21 mmol) was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (0.105 mL, 0.21 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 25 mg (43%) of the title compound of EXAMPLE 5 as an off white powder. 1H NMR (d6-dmso): δ 7.12 (d, 1H, J=7.4 Hz), 6.99 (t, 1H, J=7.3 Hz), 6.97-6.90 (m, 1H), 4.25-4.12 (m, 2H), 3.75-3.65 (m, 2H), 3.40-3.20 (m, 3H), 2.97-2.90 (m, 3H), 22.81-2.70 (m, 3H), 1.88-1.80 (m, 2H). LRMS (ES)+: 243.4 (M+H)+.

Provenance & Evidence