Water → HCID 58557147, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-cyclohexyl-7-tosyl-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridine (0.132 g, 0.323 mmol) in 1,4-dioxane (2.2 mL) was added aqueous NaOH (2 N, 0.32 mL, 0.65 mmol). The reaction was heated at about 80° C. for about 96 h. Aqueous NaOH (5 N, 0.129 mL, 0.646 mmol) was added and the reaction was continued at about 80° C. for about 18 h. Aqueous NaOH (5 N, 0.065 mL, 0.323 mmol) was added and the reaction mixture was heated at about 100° C. for about 4 h. The reaction was cooled to ambient temperature, EtOAc and water were added (5 mL each) and the layers were separated. The aqueous layer was extracted with EtOAc (2×5 mL) and the combined organics were washed with water and brine (5 mL each), dried over anhydrous Na2SO4, filtered, and concd under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% (95/4.5/0.5) DCM/MeOH/DEA in DCM to give 1-cyclohexyl-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-h][1,6]naphthyridine (0.052 g, 64%) as a tan solid: LC/MS (Table 1, Method b) Rt=1.88 min; MS m/z: 256 (M+H)+.

Provenance & Evidence