[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[CH2:8][CH2:7]2.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:9]2[CH2:8][CH2:7][C:6]3[C:11](=[C:2]([NH:1][CH2:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[CH:3]=[CH:4][CH:5]=3)[C:10]2=[O:12])=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]To a solution of the amine (Step E) and CH2Cl2 (5 mL) was added 4-pyridinecarboxaldehyde and NaBH(OAc)3. The reaction was stirred at RT for 18 h. Purification by silica flash chromatography (25-75% EtOAc:hexane) gave the desired product as a light-yellow oil. MS m/e 386 (M+H)+. Calc'd for C25H27N3O-385.50.
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