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

HRID 451848

Reaction equation

HRID 451848 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-2f6048919f944ce0b3fcb4e645122afa
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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