Methanol → HCID 86653596, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4RS,6RS)-4-((tert-butyldiphenyl-silyloxy)methyl)-6-(4-chloro-3-(trifluoromethyl)phenyl)-6-methylcyclohex-1-enyl trifluoromethane-sulfonate (816 mg, 1.086 mmol) in DMF (4.5 mL) was treated with methanol (1.762 mL, 43.4 mmol) and N,N-diisopropylethylamine (0.569 mL, 3.26 mmol), and bubbled with nitrogen for 5 min. The resulting mixture was treated with dppf (48.2 mg, 0.087 mmol) and palladium (II) acetate (19.51 mg, 0.087 mmol). The resulting solution was bubbled with carbon monoxide for 5 min, and then stirred under a carbon monoxide balloon at 60° C. for 6 h. At the conclusion of this period, the mixture was cooled to rt and diluted with ethyl acetate. The resulting mixture was washed with 1 M aqueous HCl, twice with water, once with saturated aqueous sodium chloride, dried over sodium sulfate and then concentrated under vacuum to yield a residue. The residue was purified by column chromatography on silica gel, eluting with 0-15% ethyl acetate-hexane, to provide methyl (4RS,6RS)-4-((tert-butyldiphenylsilyloxy)-methyl)-6-(4-chloro-3-(trifluoromethyl)phenyl)-6-methyl-cyclohex-1-enecarboxylate as a colorless gum (498 mg, 76%). 1H NMR (400 MHz, CDCl3) δ 7.53 (m, 5 H), 7.36 (m, 7 H), 7.26 (m, 2 H), 3.65 (s, 3 H), 3.43 (d, J=5.3 Hz, 2 H), 2.33 (m, 1 H), 1.98 (ddd, J=19.5, 10.4, 2.4 Hz, 8 H), 1.77 (m, 1 H), 1.62 (s, 3 H), 1.48 (m, 2 H), 0.97 (s, 9 H).

Provenance & Evidence