Reacción #48334

Ecuación de reacción

(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

diphenylphosphoryl azide

1,8-diazabicyclo(5.4.0)undec-7-ene

→

title compound

(4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction was stirred at the same temperature for 2 h
2. 2
   Otroto quench
3. 3
   Otrothe reaction
4. 4
   ExtracciónThe resulted mixture was extracted with EtOAc
5. 5
   LavadoThe organics were washed with brine
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe residue was purified on a silica gel column (5-20% EtOAc/hexane)

Procedimiento

To a cooled (ice bath) solution of (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol (277 mg, 890 μmol) was added drop wise diphenylphosphoryl azide (249 μl, 1158 μmol). After stirring 20 min, 1,8-diazabicyclo(5.4.0)undec-7-ene (173 μl, 1158 μmol) was added drop wise. The reaction was stirred at the same temperature for 2 h, then stirred 15h at ambient temperature. Water was added to quench the reaction. The resulted mixture was extracted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column (5-20% EtOAc/hexane) to afford the title compound. MS m/z: 308(M−N2).

Fuente