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

HRID 8482Notes

Reaction equation

HRID 8482 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[CH:15][C:9]=1[NH:10][C@@H:11]([CH3:14])[CH2:12][OH:13]>CN(C=O)C>[F:20][C:17]1[CH:16]=[CH:15][C:9]2[NH:10][C@@H:11]([CH3:14])[CH2:12][O:13][C:8]=2[C:18]=1[F:19]

Participants

4

Reactant 2

HCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 11041424(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To DMF (2 ml) was added potassium tertiary-butoxide (110 mg) under ice-cooling. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped thereinto and the obtained mixture was stirred for 30 minutes. After treating in a conventional manner, the mixture was subjected to silica gel column chromatography to give 72 mg (79%) of the title compound. The optical purity determined by HPCL was >94% ee. Various spectral data was identical with those of a specimen synthesized separately.

Workup

  1. temperaturecooling
  2. additionAfter treating in a conventional manner

Sources & evidence

ORD record
ord-660669f44f7a4e25a072a55d2b7faf91
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Reaction notes

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