Acetone → 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta thiophene-4,5-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[4-(4-chlorophenyl)-7,8-dihydro-6H-cyclohepta[b]thien-2-yl]pyridine (304.0 mg, 0.899 mmol) in tert-butyl alcohol (2.06 mL, 21.5 mmol) were added water (3.43 mL) and acetone (20.56 mL). N-methylmorpholine N-oxide (210.8 mg, 1.79 mmol) and 4% osmium tetroxide in water (0.164 mL, 0.0269 mmol) were added and the resulting pinkish suspension was heated at 50° C. for 3 hr. The reaction mixture was allowed to cool to rt and then diluted with ethyl acetate (15 mL) and water (10 mL), the organic layer was separated and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with brine (10 mL) then dried over anhydrous MgSO4, Insoluble materials were removed by filtration and then the filtrate was concentrated and the obtained residue was purified by column chromatography (SiO2, elution with 0-20% MeOH/DCM) to give the title compound as a yellow foam (241.8 mg, 72% yield). LCMS: (FA) ES+ , 372/374. 1H NMR (400 MHz, DMSO) δ 8.50 (dd, J=4.6, 1.6 Hz, 2H), 7.49 (d, J=13.4 Hz, 1H), 7.44 (dd, J=4.6, 1.6 Hz, 2H), 7.38 (d, J=8.6 Hz, 2H), 7.25 (d, J=8.6 Hz, 2H), 5.75 (s, 1H), 5.71 (s, 1H), 4.83 (d, J=4.8 Hz, 1H), 4.14 (t, J=5.1 Hz, 1H), 2.93 (dd, J=15.7, 3.9 Hz, 1H), 2.75-2.55 (m, 1H), 2.05-1.73 (m, 2H), 1.52 (d, J=3.7 Hz, 1H), 1.38 (t, J=12.9 Hz, 1H).

Provenance & Evidence