Triphenylphosphine → N-isopropyl-4,4-diphenyl-2-cyclopentenylamine
Reaction equation
[C:1]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH:10]([N:12]=[N+]=[N-])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:26]=CC=C[CH:22]=1>CC(C)=O>[CH:21]([NH:12][CH:10]1[CH2:11][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)([CH3:26])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4,4-diphenyl-2-cyclopentenyl azide (0.30 g) in acetone (3 ml) was added triphenylphosphine (0.33 g) at room temperature and refluxed for 21 hours. After being cooled, the solvent was removed under reduced pressure and a solution of sodium borohydride (0.22 g), in methanol (3 ml) was added thereto. After being stirred for 20 minutes, brine and ethyl acetate were added. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-isopropyl-4,4-diphenyl-2-cyclopentenylamine (0.26 g).