Sodium hydride → 4-(3,4-Difluorophenyl)-5-methyl-oxazolidin-2-one

HRID 1167715ノート

反応式

HRID 1167715 の反応式
C([O:5][C:6](=[O:20])[NH:7][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=1)[CH:9](O)[CH3:10])(C)(C)C.[H-].[Na+]>O>[F:19][C:14]1[CH:13]=[C:12]([CH:8]2[CH:9]([CH3:10])[O:20][C:6](=[O:5])[NH:7]2)[CH:17]=[CH:16][C:15]=1[F:18]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 22048785[1-(3,4-Difluorophenyl)-2hydroxy-propyl]-carbamic acid-tert-butyl ester

生成物 1

HCID 220486254-(3,4-Difluorophenyl)-5-methyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
35 °C

実験手順

To a well stirred solution of [1-(3,4-difluorophenyl)-2-hydroxy-propyl]-carbamic acid-tert-butyl ester (0.43 g, 1.5 mmol) THF (20 mL) was added 95% NaH (0.09 g, 3.8 mmol) at room temperature. The resulting suspension was stirred for 3 h at about 35° C. (warm water bath) and then quenched carefully with ice. The biphasic mixture was extracted with 100 mL of EtOAc, washed with brine, dried over Na2SO4, filtered and the solvent was removed in vacuo. The two diastereomers were separated by column chromatography over silica gel (First isomer: 0.11 g, Rf=0.6, 3:1 hexane-EtOAc; second isomer: 0.23 g, Rf=0.5, 3:1 hexane-EtOAc). NOE experiment suggested that the first diastereomer had the methyl and the aryl group in trans configuration while the second diastereomer had cis relationship between the two groups.

後処理

  1. customquenched carefully with ice
  2. extractionThe biphasic mixture was extracted with 100 mL of EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe two diastereomers were separated by column chromatography over silica gel (First isomer: 0.11 g, Rf=0.6, 3:1 hexane-EtOAc; second isomer: 0.23 g, Rf=0.5, 3:1 hexane-EtOAc)

出典と根拠

ORDレコード
ord-14a78f8886184af0b9c20c104db3e696
出典データセット
uspto-grants-2003_09
特許番号
US06620815B1

反応ノート

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