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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 8481Generated: October 25, 2026

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

https://huagongshe.com/reaction/8481

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 11401466—
SolventDimethylformamideHCID 6228—
Product(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineHCID 1104142466.5%

Reaction Conditions

Temperature60 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07087778B2
Source datasetuspto-grants-2006_08
ORD IDord-db2c78a2be8b4889be10b76ac296dc5d
Source noteuspto-grants-2006_08