Reaction #1379899

Reaction equation

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

triethylamine

acryloyl chloride

→

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

Yield 28.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas slowly added over a period of 1 hour to the cooled solution
2. 2
   OtherThe ice bath was removed after 4 hours
3. 3
   workup.WAITthe reaction mixture was left
4. 4
   Temperaturewarmed up gradually to room temperature
5. 5
   workup.ADDITIONWater (100 mL) was added to the reaction
6. 6
   Otherthe layers were separated
7. 7
   WashThe 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
   DryingThe organic layer was then dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Otherthe solvent removed under reduced pressure
11. 11
    OtherThe residue was purified by flash chromatography
12. 12
    workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
13. 13
    Washto elute the product
14. 14
    OtherThe purification

Procedure

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.

Source