2-(4-Iodophenyl)-2-methylpropanenitrile → 2-(4-((S)-((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(hydroxy)methyl)phenyl)-2-methylpropanenitrile

HRID 573706Notes

Reaction equation

HRID 573706 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]([CH3:23])[CH3:22])[C:12]([CH:24]=[O:25])=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][C:31]([C:34]([CH3:38])([CH3:37])[C:35]#[N:36])=[CH:30][CH:29]=1>O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:22])[CH3:23])[C:12]([C@@H:24]([OH:25])[C:28]3[CH:33]=[CH:32][C:31]([C:34]([CH3:38])([CH3:37])[C:35]#[N:36])=[CH:30][CH:29]=3)=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 665799502-(4-Iodophenyl)-2-methylpropanenitrileHCID 86662512(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde

Product 1

HCID 667621622-(4-((S)-((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(hydroxy)methyl)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and 2-(4-iodophenyl)-2-methylpropanenitrile. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride complex in tetrahydrofurane is used instead of isopropylmagnesium chloride.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-e31726c09f9640cbaa10a9e2af2c4900
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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