Ammonium Chloride → HCID 45486473, compound

Participants

Reaction Steps

To a stirred solution of the above ((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(thiophen-2-yl)methanone was added methylmagnesium bromide solution (3 M in diethyl ether, 2 mL, 6 mmol) dropwise at −78° C. under argon. The reaction mixture was then stirred at RT for 2.5 hr before saturated aqueous ammonium chloride solution (6 mL) was added slowly with water bath cooling. The mixture was extracted with ethyl acetate (3×5 mL). The combined organic solutions were dried (Na2SO4) and concentrated. Silica gel flash chromatography (10-100% ethyl acetate in hexanes) gave (S)-1-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)-1-(thiophen-2-yl)ethanol (58 mg, 0.14 mmol, 49% yield for steps (h)+(i)+(j)) as a solid.

Provenance & Evidence