Potassium Hydroxide → 3',4'-dihydro-2-oxospiro[piperidine-4,4'(1H)-quinoline]
Reaction equation
F[C:2](F)(F)[C:3]([NH2:5])=[O:4].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)C(=O)C2)[CH2:10][CH2:9]1.[OH-].[K+]>CO.O>[O:4]=[C:3]1[CH2:2][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:8][CH2:9][CH2:10]2)[CH2:12][CH2:13][NH:5]1Participants
4
Procedure
A solution of 49 mg (0.157 mmol) of the high RF material from Step B in methanol/water 4:1 with excess potasium hydroxide was stirred over night. The solution was concentrated and water and ethyl acetate were added to the residue. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to give 31 mg (0.143 mmol) of the title compound.