4-Bromo-3-fluorobenzotrifluoride → (R)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-(3,6-dihydro-2H-pyran-4-yl)-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(2-fluoro-4-(trifluoromethyl)phenyl)methanol

HRID 573760Notes

Reaction equation

HRID 573760 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]([C:27]3[CH2:28][CH2:29][O:30][CH2:31][CH:32]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=1[F:44]>O1CCCC1>[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]([C@H:25]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=3[F:44])[OH:26])=[C:11]([C:27]3[CH2:28][CH2:29][O:30][CH2:31][CH:32]=3)[C:10]1=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 86662519(S)-5'-(tert-butyldimethylsilyloxy)-4'-(3,6-dihydro-2H-pyran-4-yl)-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-carbaldehyde

Product 1

HCID 66762345(R)-((S)-5'-(tert-butyldimethylsilyloxy)-4'-(3,6-dihydro-2H-pyran-4-yl)-2'-isopropyl-6',8'-dihydro-5'H-spiro[cyclobutane-1,7'-quinoline]-3'-yl)(2-fluoro-4-(trifluoromethyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Obtained by starting from (S)-5′-(tert-butyldimethylsilyloxy)-4′-(3,6-dihydro-2H-pyran-4-yl)-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carbaldehyde and 1-bromo-2-fluoro-4-(trifluoromethyl)benzene. Tetrahydrofurane is used instead of toluene.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-0e70354458264b91a82ddef192de1b0e
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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