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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 8482Generated: October 25, 2026

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

https://huagongshe.com/reaction/8482

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S)-2-(2,3,4-Trifluoroanilino)propanolHCID 11401466—
ReactantPotassium tert-butoxideHCID 23665647—
SolventDimethylformamideHCID 6228—
Product(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineHCID 1104142479.8%

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07087778B2
Source datasetuspto-grants-2006_08
ORD IDord-660669f44f7a4e25a072a55d2b7faf91
Source noteuspto-grants-2006_08