Reacción #1379899

Ecuación de reacción

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

triethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyl),N-(tert-butoxycarbonyloxy)acrylamide

Rendimiento 28.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas slowly added over a period of 1 hour to the cooled solution
2. 2
   OtroThe ice bath was removed after 4 hours
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Temperaturawarmed up gradually to room temperature
5. 5
   workup.ADDITIONWater (100 mL) was added to the reaction
6. 6
   Otrothe layers were separated
7. 7
   LavadoThe organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL)
8. 8
   SecadoThe organic layer was then dried over magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Otrothe solvent removed under reduced pressure
11. 11
    OtroThe residue was purified by flash chromatography
12. 12
    workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
13. 13
    Lavadoto elute the product
14. 14
    OtroThe purification

Procedimiento

A solution of acryloyl chloride (700 μL; 779.8 mg; 8.6 mmole) dissolved in dry dichloromethane (20 mL) was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) (2.0038 g; 8.6 mmole) and triethylamine (1.32 mL; 958.3 mg; 9.5 mmole) in dry dichloromethane (20 mL) was slowly added over a period of 1 hour to the cooled solution. The ice bath was removed after 4 hours and the reaction mixture was left stirring overnight while its temperature warmed up gradually to room temperature. Water (100 mL) was added to the reaction and the layers were separated. The organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL). The organic layer was then dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate (90:10) to elute the product. The purification gave 690 mg (28%) of N-(tert-butoxycarbonyl),N-(tert-butoxycarbonyloxy)acrylamide (32) as a colorless oil.

Fuente