Hydrochloric Acid → HCID 131724547, compound

Participants

Reaction Steps

To a solution of (±)-cis-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline free base from EXAMPLE 109 (140 mg, 0.70 mmol) in 10 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.125 mL, 1.4 mmol) and sodium triacetoxyborohydride (0.45 g, 2.1 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 (1.05 mL, 2.1 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 100 mg (50%) of the title compound of EXAMPLE 110 as an off white powder LRMS (ES)+: 214.9 (M+H)+.

Provenance & Evidence