Reaktion #1379896

Reaktionsgleichung

Water

tert-butyl N-(tert-butoxycarbonyloxy)carbamate

N,N-diisopropylethylamine

acryloyl chloride

→

N-(tert-butoxycarbonyloxy)acrylamide

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe layers were separated
3. 3
   WaschenThe organic solution was washed with diluted hydrochloric acid
4. 4
   TrocknenThe organic layer was dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solvent removed under reduced pressure
7. 7
   SonstigeThe residue was purified by flash chromatography
8. 8
   workup.ADDITIONa mixture of hexane and ethyl acetate (90:10)
9. 9
   SonstigeThe purification

Vorschrift

A solution of acryloyl chloride dissolved in dry dichloromethane was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) and N,N-diisopropylethylamine in dry dichloromethane was added. Water was added after 16 hours of reaction and the layers were separated. The organic solution was washed with diluted hydrochloric acid, a saturated sodium bicarbonate solution, water, and brine. The organic layer was 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). The purification gave N-(tert-butoxycarbonyl), N-(tert-butoxycarbonyloxy)acrylamide (32).

Quelle