[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[CH:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[CH2:23]2)[CH2:29]3)=[CH:17][CH:16]=1)=O.[OH-].[Na+]>O>[CH3:12][NH:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]23[CH2:31][CH:26]4[CH2:25][CH:24]([CH2:30][CH:28]([CH2:27]4)[CH2:29]2)[CH2:23]3)=[CH:19][CH:20]=1To a stirred suspension of 1.30 g. LiAlH4 in 20 ml. THF there was added 9.17 g. (0.034 mole) of N-formyl-p-(1-adamantyloxy)aniline in 200 ml. THF. Following 8 hours heating at reflux the mixture was cooled in ice and treated in turn with 1.3 ml. each of H2O and 15% NaOH and 4.9 ml. H2O. The inorganic gel was removed on a filter and the filtrate taken to dryness. The residue was recrystallized from Me2CO:SSB to give 5.96 g. (79%) of amine, N-methyl-p(1-adamantyloxy)aniline m.p. 134°-136°.
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