Methanol → HCID 86653603, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4RS,6RS)-4-(benzyloxy)-6-(4-chloro-3-(trifluoromethyl)phenyl)-6-methylcyclohex-1-enyl trifluoromethanesulfonate (91 mg, 0.172 mmol) in DMF (1 mL) was treated with triphenylphosphine (9 mg, 34 μmol), methanol (279 μl, 6.88 mmol) and triethylamine (48 μl, 344 μmol). The resulting mixture was bubbled with nitrogen for 5 min and then palladium (II) acetate (4 mg, 17 μmol) was added. Upon completion of addition, the resulting solution was bubbled with carbon monoxide for 5 min and then stirred under a carbon monoxide balloon at 70° C. for 23 h. After this time, the mixture was cooled to rt and diluted with ether. The resulting mixture was washed twice with water and once with 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 5-50% ethyl acetate-hexanes, to provide methyl (4RS,6RS)-4-(benzyloxy)-6-(4-chloro-3-(trifluoromethyl)phenyl)-6-methylcyclohex-1-enecarboxylate as a yellow gum (59 mg, 78%). Mass spectrum m/z 456 (M+NH4+), 492 (M+OAc−). 1H NMR (400 MHz, CDCl3) δ 1.68 (s, 3 H) 1.80 (dd, J=12.7, 11.2 Hz, 1 H) 1.98-2.06 (dm, J=12.7 Hz, 1 H) 2.28 (ddd, J=19.0, 9.0, 3.1 Hz, 1 H) 2.65-2.74 (dtd, J=18.8, 5.1, 1.5 Hz, 1 H) 3.28-3.37 (m, 1 H) 3.63 (s, 3 H) 4.32-4.41 (ab, J=11.7 Hz, 2 H) 7.11-7.14 (m, 2 H) 7.16 (dd, J=5.3, 2.8 Hz, 1 H) 7.21-7.28 (m, 3H) 7.32-7.40 (m, 2 H) 7.49 (d, J=2.0 Hz, 1 H).

Provenance & Evidence