Pyridine → methyl 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylate

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Reaction Steps

The above methyl 5-(((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)(hydroxy)methyl)thiophene-2-carboxylate was dissolved in anhydrous methylene chloride (3 mL). Pyridine (0.1 mL) and then Dess-Martin periodinane (204 mg, 0.48 mmol) were added. The reaction mixture was stirred at RT for 1 hr and quenched by the addition of saturated aqueous sodium bicarbonate solution (5 mL) and saturated aqueous sodium thiosulfate solution (2.5 mL). The mixture was stirred at RT for 30 min. The aqueous layer was separated and extracted with methylene chloride (2×2 mL). The combined organic solutions were dried (Na2SO4). Silica gel flash chromatography (20-100% ethyl acetate in heptanes) gave methyl 5-((5aR,6S)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinoline-6-carbonyl)thiophene-2-carboxylate (113 mg, 0.25 mmol, 78% yield for steps (b)+(c)) as a solid. MS found: (M+H)+=451.1.

Provenance & Evidence