Hydrochloric Acid → HCID 131724527, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans-10-benzyl-5,6,9,10,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinolin-8(8aH)-one from EXAMPLE 1, Part E (1.2 g, 3.8 mmol) in 20 mL of toluene was added 1-chloroethyl chloroformate (0.81 mL, 7.53 mmol) and the resulting solution was stirred at 110° C. for 3 h. The reaction mixture was cooled and the toluene was removed under reduced pressure. The residue was taken up in 20 mL of methanol and was stirred at 65° C. for 1 h. The reaction was cooled and the methanol was removed under reduced pressure. A portion of the residue (50 mg, 0.19 mol) 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 ether and there was added 2M HCl in ether (0.095 mL, 0.19 mmol). The solvent was decanted and the remaining solid was triturated twice with ether and was dried in vacuo to afford 25 mg (50%) of the title compound of EXAMPLE 3 as an off white powder. LRMS (ES)+: 270.3 (M+H+CH3CN)+.

Provenance & Evidence