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

HRID 2187552노트

반응식

HRID 2187552 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)-2hydroxy-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 NaSO4, 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 NaSO4
  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-b2bac6e078ea4133896142bb07cd490f
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410554B1

반응 노트

불러오는 중…