Tetraethylammonium fluoride hydrate → (S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate

HRID 451974

반응식

HRID 451974 반응식
[Si](O[CH2:9][C@H:10]([CH2:26][CH2:27][CH2:28][O:29]S(C)(=O)=O)[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(C(C)(C)C)(C)C.O.[F-].C([N+](CC)(CC)CC)C>C1COCC1.CCOC(C)=O>[CH3:17][C:14]1([CH3:18])[N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@@H:12]([CH2:11][C@H:10]2[CH2:26][CH2:27][CH2:28][O:29][CH2:9]2)[CH2:16][O:15]1

참가 물질

5

반응물 2

HCID 16211652Tetraethylammonium fluoride hydrateHCID 58011555(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-((methylsulfonyl)oxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate

생성물 1

HCID 58011520(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate수율 54%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(methylsulfonyloxy)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (37.7 g, 74.2 mmol) in THF (1000 mL) was added tetraethylammonium fluoride hydrate (41 g, 185.5 mmol) in portions. The reaction mixture was stirred under reflux overnight. The mixture was diluted with EtOAc (1000 mL), washed with water (300 mL) and brine (500 mL). The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified by column chromatography to afford (S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (12.0 g, 54%).

후처리

  1. temperatureunder reflux overnight
  2. washwashed with water (300 mL) and brine (500 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product, which
  7. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-3b1bdec1d4114b0b8786a78e2c932f4f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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