[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34][CH3:35])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([NH:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:38](O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34][CH3:35])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([N:26]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH3:38])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1To a solution of methyl 14-cyclohexyl-7-{[2-(dimethylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 9, Step 5) in DCM (0.1 M), was added formaldehyde (3.0 eq) and acetic acid (5.5 eq), followed by sodium cyanoborohydride (3 eq). NaOH (20 eq, 1 N) was added after 2 h, and after stirring for 5 min the mixture was taken into EtOAc and washed with water and brine. Drying over sodium sulfate and concentration in vacuo gave the crude product, which was used without further purification; MS (ES+) m/z 490 (M+H)+.
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