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

HRID 1167715노트

반응식

HRID 1167715 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
35 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-14a78f8886184af0b9c20c104db3e696
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620815B1

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