Trifluoroacetic acid → 2-((5aR,6R)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)acetic acid

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Reaction Steps

To a stirred mixture of 2-((5aR,6R)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)-1-methoxyethanol (Example 5a, 90 mg, 0.25 mmol), 2-methylbut-2-ene (2 M in THF, 1 mL), tert-butanol (0.5 mL) and trifluoroacetic acid (0.03 mL, 0.4 mmol) was added a solution of sodium chlorite (80%, 70 mg, 0.62 mmol) and sodium dihydrogenphosphate monohydrate (80 mg, 0.58 mmol) in water (0.6 mL) at 0° C. The reaction mixture was then stirred at RT for 1.5 hr. The aqueous layer was separated, extracted with THF (1.5 mL), neutralized with solid sodium bicarbonate to pH=6, and extracted with THF (2×1 mL). The combined organic solutions were dried (Na2SO4) and concentrated to give 2-((5aR,6R)-1-(4-fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)acetic acid (195 mg) which was used in the next step without further purification. MS found: (M+H)+=341.2.

Provenance & Evidence