Trifluoroacetic acid → HCID 44538420, compound

Participants

Reaction Steps

A solution of the product from Example 7A (28 mg, 0.065 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (0.2 mL) at ambient temperature and stirred for 16 hours. The mixture was diluted with dichloromethane (20 mL), and basified with sodium hydroxide (1 N). The organic layer was separated, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a silica gel column eluting with ammonium hydroxide/methanol/dichloromethane (0.8/8/92) to provide the dehydrogenated material as the major product and title compound: 1H NMR (CD3OD) δ 1.00-1.18 (m, 1H), 1.27-1.41 (m, 1H), 1.45-1.58 (m, 1H), 1.62-1.75 (m, 2H), 1.92-2.07 (m, 3H), 2.11-2.24 (m, 1H), 2.24-2.39 (m, 2H), 3.38-3.52 (m, 1H), 3.74-3.92 (m, 2H), 3.98-4.12 (m, 1H), 4.10-4.24 (m, 2H), 6.87 (d, 1H), 8.08 (d, 1H); MS (DCl/NH3) m/z 326 (M+H)+.

Provenance & Evidence