Hydrochloric Acid → HCID 68525020, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-cis ethyl 9-benzyl-7-oxo-4,5,8,9,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-7a(7H)-carboxylate (3.9 g, 10.4 mmol) in 50 mL of 1,4-dioxane was added 50 mL of 3N HCl and the resulting mixture was stirred at 100° C. for 24 h. The dioxane and most of the water was removed in vacuo, and the residue was basified with sat'd aq Na2CO3 and extracted with ethyl acetate. The layers were separated and the organics were washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 3.1 g (96%) of (±)-cis-9-benzyl-4,5,8,9,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinolin-7(7aH)-one free base, which was sufficiently pure to be used without purification. LRMS (ES)+: 305.1 (M+H)+. A portion of this material (50 mg, 0.16 mmol) was dissolved in 5 mL of ether and 1 mL of absolute ethanol. Then there was added 2M HCl in ether (0.165 mL, 0.33 mmol). The resulting solid was filtered, washed twice with ether and dried in vacuo to afford the title compound of EXAMPLE 107 as a pale yellow powder. 1H NMR (dmso-D6) δ: 7.60-7.50 (m, 2H), 7.48-7.38 (m, 3H), 7.19-7.15 (m, 1H), 7.12-7.07 (m, 1H), 6.98-6.90 (m, 1H), 4.45-4.37 (m, 1H), 4.30-4.18 (m, 1H), 4.02-3.90 (m, 2H), 3.87-3.77 m, 2H), 3.68-3.40 (m, 3H), 3.21-3.05 (m, 3H). LRMS (ES)+: 305.1 (M+H)+.

Provenance & Evidence