Sodium hydride → 6-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 2091513Notes

Reaction equation

HRID 2091513 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C@@H:3]([N:5]([CH2:9][CH2:10][C:11]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([OH:15])[CH2:12][CH:13]=[CH2:14])[C:6](=O)[O-:7])[CH3:4].[H-].[Na+]>C1COCC1>[CH2:12]([C:11]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:15][C:6](=[O:7])[N:5]([C@H:3]([C:2]([CH3:24])([CH3:23])[CH3:1])[CH3:4])[CH2:9][CH2:10]1)[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86658725(S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carba mate

Product 1

HCID 584852576-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3,3-dimethylbutan-2-yl(3-(4-fluorophenyl)-3-hydroxyhex-5-enyl)carba-mate (2.2 g, 6.27 mmol) in dry THF (25 mL) was added NaH (752 mg, 18.80 mmol) at 0° C. under N2, and the mixture was stirred at rt overnight. The reaction was quenched with water, and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford the crude product, which was purified by chromatography to give two isomers of 6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude product, which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-28124d31564e47cdbf0b4c9ea76c1b1e
Source dataset
uspto-grants-2013_05
Patent number
US08440658B2

Reaction notes

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