Ethyl bromoacetate → 1-{3-[(4'-Fluoro[1,1'-biphenyl]-4-yl)sulfonyl]-2-hydroxypropyl}-4,4-dimethyl-2,6-piperidinedione

HRID 1597425Notes

Reaction equation

HRID 1597425 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:18][C:19]1([CH3:27])[CH2:25][C:24](=[O:26])[NH:23][C:21](=[O:22])[CH2:20]1.Br[CH2:29][C:30](OCC)=[O:31]>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH2:1][CH:30]([OH:31])[CH2:29][N:23]3[C:24](=[O:26])[CH2:25][C:19]([CH3:27])([CH3:18])[CH2:20][C:21]3=[O:22])(=[O:4])=[O:3])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 142924,4-Dimethylpiperidine-2,6-dioneHCID 160868644-(4'-Fluorophenyl)-phenyl methyl sulfone

Product 1

HCID 217000651-{3-[(4'-Fluoro[1,1'-biphenyl]-4-yl)sulfonyl]-2-hydroxypropyl}-4,4-dimethyl-2,6-piperidinedione

Procedure

Reaction of 4-(4′-fluorophenyl)-phenyl methyl sulfone with ethyl 3,3-dimethylglutarimideacetate (prepared from 3,3-Dimethylglutarimide and ethyl bromoacetate (as in Example 120A) following the procedures of Example 126A, followed by reduction as described in Example 126B afforded the two title products which were chromatographically separated to give the desired products.

Workup

  1. customafforded the two title products which
  2. customwere chromatographically separated

Sources & evidence

ORD record
ord-143eb7e78acf4da381a50e842631a733
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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