Reaction #8578

Reaction equation

compound

(2S)-2-(2,3,4-Trifluoroanilino)-1-propanol

potassium tertiary-butoxide

→

title compound

Yield 79.8%

(3S)-(+)-7,8-Difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine

Yield 79.8%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.ADDITIONAfter treating in a conventional manner

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.

Source