5-Iodo-2-(trifluoromethyl)benzonitrile → 5-((S)-((S)-5-(tert-butyldimethylsilyloxy)-4-(3,6-dihydro-2H-pyran-4-yl)-7,7-dimethyl-2-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydroquinolin-3-yl)(hydroxy)methyl)-2-(trifluoromethyl)benzonitrile

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:12]([CH:27]=[O:28])=[C:11]([C:29]3[CH2:30][CH2:31][O:32][CH2:33][CH:34]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:36]1[CH:37]=[CH:38][C:39]([C:44]([F:47])([F:46])[F:45])=[C:40]([CH:43]=1)[C:41]#[N:42].C([Mg]Cl)(C)C.[Cl-].[Li+].C([Mg]Cl)(C)C>O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[C:12]([C@@H:27]([OH:28])[C:36]3[CH:37]=[CH:38][C:39]([C:44]([F:45])([F:46])[F:47])=[C:40]([CH:43]=3)[C:41]#[N:42])=[C:11]([C:29]3[CH2:30][CH2:31][O:32][CH2:33][CH:34]=3)[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]