Ethyl Acetate → HCID 11611666, compound

Participants

Reaction Steps

To a solution of 1,1,1-trifluoro-3-[(2-methyl-5-quinolinyl)imino]-2-[(1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-2-propanol (intermediate 8) (130 mg, 0.30 mmol) in glacial acetic acid (4 ml) stirred under nitrogen at 21° C., was added sodium triacetoxyborohydride (254 mg, 1.2 mmol) portionwise over 25 min and the solution was stirred for a further 4 h. The solution was then carefully added to a mixture of saturated aqueous sodium carbonate (50 ml) and ethyl acetate (30 ml) and stirred for 10 min, when effervescence had finished. The layers were separated and the aqueous layer re-extracted with ethyl acetate (30 ml) and the combined organic layers were washed with saturated sodium carbonate (15 ml), water (2×30 ml) and saturated brine (30 ml), dried over anhydrous sodium sulphate and evaporated. The crude product was purified on a 50 g silica cartridge using a Flashmaster 2 system with a 0-100% gradient of ethyl acetate in cyclohexane over 80 min to give the title compound (91.6 mg, 71%) as a mixture of diastereomers.

Provenance & Evidence