(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde → HCID 66761325, compound

HRID 573753Notes

Reaction equation

HRID 573753 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].[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35]([Mg]Br)=[CH:34][CH:33]=1)([CH3:30])([CH3:29])[CH3:28].FC1C=CC([Mg]Br)=CC=1>O1CCCC1>[C:27]([O:31][C:32]1[CH:37]=[CH:36][C:35]([C@@H:24]([C:12]2[C:13]([CH:21]([CH3:22])[CH3:23])=[N:14][C:15]3[CH2:16][C:17]([CH3:19])([CH3:20])[CH2:18][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[C:10]=3[C:11]=2[I:26])[OH:25])=[CH:34][CH:33]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 86662512(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehydeHCID 178418676HCID 178418676, compoundHCID 178450188HCID 178450188, compound

Product 1

HCID 66761325HCID 66761325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde. A 0.5 M solution of (4-tert-butoxyphenyl)magnesium bromide in tetrahydrofurane is used instead of 1 M solution of 4-fluorophenyl-magnesium bromide in tetrahydrofurane.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-e30c66d9403541b9967a427cca03a5c9
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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