Water → HCID 44612585, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl 5-(4-chloro-3-(trifluoromethyl)phenyl)-4-hydroxy-5-methylcyclohex-3-ene-1,3-dicarboxylate (mixture of diastereomers, 485 mg, 1.192 mmol) in DMSO (5 mL) was treated with sodium chloride (139 mg, 2.385 mmol) and water (0.107 mL, 5.96 mmol). The resulting mixture was bubbled with nitrogen for 15 min, and then heated under nitrogen on an oil bath at 150-160° C. for 4.5 h. After this time, the mixture was cooled to rt, diluted with water and then extracted three times with ethyl acetate. The combined organic layers were washed with water followed by saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under vacuum to yield a residue. The residue was purified by column chromatography on silica gel, eluting with 20-35% ethyl acetate-hexanes, to provide methyl (1RS,3RS)-3-(4-chloro-3-(trifluoromethyl)-phenyl)-3-methyl-4-oxocyclohexanecarboxylate (137 mg, 33%) and methyl (1SR,3RS)-3-(4-chloro-3-(trifluoro-methyl)phenyl)-3-methyl-4-oxocyclohexanecarboxylate (188 mg, 45%). The (1SR, 3RS) diastereomer could be partially converted to the (1RS, 3RS) diastereomer as described in the procedure of Example 7, Part 3.

Provenance & Evidence