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

HRID 8483Notes

Reaction equation

HRID 8483 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.[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 5360545SodiumHCID 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 99.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(3S)-7,8-Difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine·p-toluenesulfonate (1 g) was suspended in AcOEt (10 ml) and then an aqueous solution of sodium hdyrogencarbonate (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 (516 mg, 99.8% ee) as a yellow oily substance.

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-3d1dc336c19c43709e300aac6fceed54
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Reaction notes

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