Triphenylphosphine → HCID 71544105, compound

Participants

Reaction Steps

A mixture of (7S,8aR)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydropyrrolo[1,2-a]pyrazin-7-ol (Example 17, 103 mg, 0.294 mmol), 5-cyclopropylpyrazin-2-ol (40 mg, 0.294 mmol) and triphenylphosphine (154 mg, 0.588 mmol) in tetrahydrofuran (1 mL) was stirred at room temperature for 1 hour. Then (E)-diisopropyl diazene-1,2-dicarboxylate (119 mg, 0.588 mmol) was added, and the reaction was continued at room temperature overnight. The solution was concentrated, and the residue was purified by chromatography on silica gel (ethyl acetate/hexane=3:2) to give the title compound (68 mg, 48% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86 (m, 4H), 1.22 (m, 2H), 2.12 (m, 4H), 2.41 (m, 2H), 3.01 (m, 2H), 3.67 (m, 1H), 3.83 (m, 1H), 5.25 (m, 1H), 7.94 (m, 1H), 8.03 (m, 1H), 8.15 (m, 4H); MS (ESI) m/z 469 (M+H)+.

Provenance & Evidence