C(OC([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)(O)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.[OH-].[Na+]>FC(F)(F)C(O)=O>[Cl:27][C:22]1[CH:21]=[C:20]([C:16]2[CH2:17][CH2:18][C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:14][CH:15]=2)[CH:25]=[CH:24][C:23]=1[Cl:26]9-(3,4-Dichloro-phenyl)-9-hydroxy-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (547 mg, 1.32 mmol) was dissolved in trifluoroacetic acid (25 mL) and heated to reflux over night. Ethyl acetate was added and the reaction mixture was basified with sodium hydroxide (2 N). The aqueous phase was extracted three times with ethyl acetate and the combined organic phase was washed with brine, dried (sodium sulfate), filtered and evaporated to give 410 mg (100%) of 9-(3,4-dichloro-phenyl)-3-aza-spiro[5.5]undec-8-ene as a white gum.
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