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

HRID 451967Notes

Reaction equation

HRID 451967 reaction equation
O[CH2:2][CH2:3][CH2:4][C@@H:5]([CH2:21][O:22]S(C1C=CC(C)=CC=1)(=O)=O)[CH2:6][C@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[H-].[Na+]>CN(C=O)C>[CH3:13][C:9]1([CH3:12])[N:8]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@@H:7]([CH2:6][C@H:5]2[CH2:4][CH2:3][CH2:2][O:22][CH2:21]2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58011504(S)-tert-butyl 4-((R)-5-hydroxy-2-(tosyloxymethyl)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 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-tert-butyl 4-((R)-5-hydroxy-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (254 mg, 0.54 mmol) in anhydrous DMF (8 mL) at 0° C. under N2 was added NaH (43 mg, 1.08 mmol). After stirred at this temperature for 1 hr, the reaction was quenched with aq. NH4Cl and then evaporated to dryness. The residue was dissolved in EtOAc and H2O, the separated aqueous phase was extracted with EtOAc. The combined organic phases were washed with H2O, brine, and dried over Na2SO4, filtered, and evaporated. The residue was purified on silica gel column to afford (S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (136 mg, 84%).

Workup

  1. customthe reaction was quenched with aq. NH4Cl
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. extractionH2O, the separated aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-60e1bbed2a684f81ad4b07a22195184a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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