Aluminium lithium hydride → HCID 69235167, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-(trifluoromethoxy)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide of Step 3 (1.22 g, 4.09 mmol) in anhydrous tetrahydrofuran kept under nitrogen, was added via syringe a 1M solution of lithium aluminum hydride in terahydrofuran (8.18 mmol). The pale yellow suspension was heated at 70° C. for 1 hour, allowed to cool to room temperature and then placed in an ice water bath. Under vigorous stirring the mixture was quenched with ethyl acetate, followed by a saturated aqueous solution of Rochelle salt. The slurry was extracted with ethyl acetate, the extracts were washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent provided a solid residue that was purified by chromatography over silica Merck 60 using a 2% to 10% gradient of methanolic ammonia in dichloromethane to provide the title compound as a white solid (0.946 g, 81.6%), m.p. 148-150° C. MS [(+)ES, m/z]: 285.1 [M+H]+. MS [(−)ES, m/z]: 283.1 [M−H]−. HRMS [(+)ESI, m/z]: 285.1212 [M+H]+. Calc'd for C14H16F3N2O: 285.1214. HPLC: Chromolith Monolith column, 0.46×10 cm, gradient of acetonitrile in water (0.01% TFA), 4 mL/min, detection at 280 nm; Rt 1.6 min.

Provenance & Evidence