Sodium hydride → (3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazine
Reaction equation
[H-].[Na+].F[C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[NH:6][C@@H:7]([CH3:10])[CH2:8][OH:9]>CN(C=O)C>[F:16][C:13]1[CH:12]=[CH:11][C:5]2[NH:6][C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:14]=1[F:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To DMF (2 ml) was added sodium hydride (39 mg) and the mixture was heated to 60° C. in an oil bath. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped therein to and the obtained mixture was stirred for 1 hour. After treating in a conventional manner, the mixture was subjected to silica gel column chromatography to give 60 mg (66%) 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
- additionAfter treating in a conventional manner
Sources & evidence
- ORD record
- ord-db2c78a2be8b4889be10b76ac296dc5d
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087778B2
Reaction notes
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