Water → tert-butyl(+/-)-cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

HRID 877240ノート

反応式

HRID 877240 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=[O:12])[NH:6][CH2:5]2.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH:31]1([CH:23]([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][N:6]3[CH2:5][C:4]4[C:8](=[CH:9][C:10]([F:11])=[C:2]([F:1])[CH:3]=4)[C:7]3=[O:12])=[CH:18][CH:19]=2)[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:35][CH2:34][CH2:33][CH2:32]1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetateHCID 213653915,6-Difluoro-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 58136606tert-butyl(+/-)-cyclopentyl{4-[(5,6-difluoro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

At 0° C., 60 mg (0.355 mmol) of 5,6-difluoro-2,3-dihydro-1H-isoindol-1-one were added to 21.3 mg (0.53 mmol, 60% pure) of sodium hydride in 1 ml of DMF. The mixture was stirred for 30 min, and 125.3 mg (0.35 mmol) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0° C. The reaction mixture was stirred for a further 2 h, and water and ethyl acetate were then added. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 2:1). This gave 30.0 mg (19.2% of theory) of the target compound.

後処理

  1. stirringThe reaction mixture was stirred for a further 2 h
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 2:1)

出典と根拠

ORDレコード
ord-3d83c711a53744f0b0e9ec1d07b2942f
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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