Sodium Bicarbonate → (3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazine

HRID 458216Notes

Reaction equation

HRID 458216 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:3]=1[F:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:3]=1[F:13]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86596419(3S)-7,8-Difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzo xazine.p-toluenesulfonate

Product 1

HCID 11041424(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineYield 124.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(3S)-7,8-Difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzo xazine•p-toluenesulfonate (1 g) was suspended in AcOEt (10 ml) and then an aqueous solution of NaHCO3 (10 ml) was added thereto. After stirring at room temperature for 1 hour, the mixture was extracted with AcOEt. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to thereby give the title compound (645.2 mg, 99.8% ee) as a yellow oily substance. Various spectral data was identical with those obtained in Example 83.

Workup

  1. extractionthe mixture was extracted with AcOEt
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f6c36c65c8d4fd38f1df8bc5f4f17d4
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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