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

HRID 218419

反応式

HRID 218419 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-479e3a46b44e46e6915724f8bf019a7f
出典データセット
uspto-grants-2012_06
特許番号
US08198453B2

関連ノート

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