Triphenylphosphine → [trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl amine

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 12B (700 mg, 2.14 mmol) in mixture of tetrahydrofuran/H2O (15 mL/1.5 mL), triphenylphosphine (1.12 mg, 4.28 mmol) was added at room temperature. The reaction mixture was heated to 65° C. for five hours. It was cooled to room temperature, concentrated under reduced pressure, azeotroped with toluene, and purified by flash chromatography (eluting with 10% methanol/CH2Cl2) to provide the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 7.41-7.48 (m, 2H), 7.28-7.35 (m, 1H), 5.72 (m, 1H), 5.26-5.38 (m, 1H), 3.93-4.04 (m, 1H), 3.17-3.42 (m, 4H), 2.72-2.84 (m, 2H). MS (DCI) m/z 301 (M+H)+.

Provenance & Evidence