Triphenylphosphine → HCID 178511702, compound

Participants

Reaction Steps

To a solution of the 1H-indazol-4-ol (131 mg, 0.977 mmol) obtained in Example 320, (b) in tetrahydrofuran (10 ml) were added dropwise cis-2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (215 mg, 0.879 mmol), triphenylphosphine (283 mg, 1.07 mmol) and 40%-dibenzyl azodicarboxylate-dichloromethane solution (0.672 ml, 1.17 mmol) at 0° C. The resulting mixture was warmed up to room temperature 30 minutes after the addition. After stirring overnight, the reaction solution was concentrated under reduced pressure and the resulting residue was dissolved in chloroform (50 ml) and washed with a 1M-aqueous sodium hydroxide solution (20 ml). Extraction with chloroform (20 ml) was carried out again, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). To the resulting mixture was added 30%-methylamine/ethanol (2 ml) at room temperature, and the resulting mixture was refluxed for 15 minutes. After 4 hours, the reaction solution was concentrated under reduced pressure at room temperature and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=10/1→chloroform/methanol/(1%-aqueous ammonia)=10/1) to obtain trans-4-(1H-indazol-4-yloxy)-cyclohexanamine (11 mg, 5.6%).

Provenance & Evidence