(S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde → (S)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(4-isopropylphenyl)methanol

HRID 573752Notes

Reaction equation

HRID 573752 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([CH:25]=[O:26])=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([Mg]Br)=[CH:33][CH:32]=1)([CH3:30])[CH3:29]>>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:23])[CH3:24])[C:12]([C@H:25]([C:34]3[CH:35]=[CH:36][C:31]([CH:28]([CH3:30])[CH3:29])=[CH:32][CH:33]=3)[OH:26])=[C:11]([I:27])[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 86662517(S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehydeHCID 178439193HCID 178439193, compound

Product 1

HCID 66762704(S)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-iodo-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(4-isopropylphenyl)methanol

Procedure

Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 4-isopropylphenylmagnesiumbromide.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-271df2485b5f4b27a4b326807ecfe569
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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