Water → Scopine Di(2-thienyl) Glycolate

HRID 14444노트

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HRID 14444 반응식
[CH3:1][N:2]1[CH:7]2[CH2:8][CH:9]([OH:11])[CH2:10][CH:3]1[CH:4]1[CH:6]2[O:5]1.C[O:13][C:14](=O)[C:15]([OH:26])([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1.[H-].[Na+].O>ClCCl>[CH3:1][N:2]1[CH:7]2[CH2:8][CH:9]([O:11][C:14](=[O:13])[C:15]([OH:26])([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:10][CH:3]1[CH:4]1[CH:6]2[O:5]1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2744399-Methyl-3-oxa-9-azatricyclo(3.3.1.02,4)nonan-7-olHCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

생성물 1

HCID 23553456Scopine Di(2-thienyl) Glycolate수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
70 °C

실험 절차

The product of step (b) (2.00 g, 12.9 mmol) and the product of step (a) (3.61 g, 14.2 mmol) were melted together at 70° C., under a vacuum of 210 Torr for 1 h. Sodium hydride (60% suspension in oil, 620 mg, 15.5 mmol) was added and the reaction mixture was stirred at 70° C. under 210 Torr for 3 h. The reaction mixture was allowed to cool to ambient temperature and then water (30 mL) and dichloromethane (30 mL) were added. The organic layer was separated and washed with water (2×20 mL), dried (magnesium sulfate), filtered and the solvent was removed under reduced pressure. The resulting residue was purified by flash chromatography (5% MeOH/DCM) to give the title compound as a solid (2.03 g, 5.4 mmol, 42%).

후처리

  1. temperatureto cool to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with water (2×20 mL)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by flash chromatography (5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-39e28322721a467dbee2fe70a9c2b8c6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732441B2

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