Reaction #1269838

Reaction equation

ethyl acrylate

ethyl glycinate hydrochloride

sodium hydroxide

→

Diethyl-2-azabutane-1,4-dicarboxylate

Solvents

water

Conditions

Workup

1. 1
   OtherAfter 19 h the solution is partitioned with dichloromethane (3×100 mL)
2. 2
   DryingThe organic layer is dried with anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   workup.DISTILLATIONThe residue is distilled
6. 6
   Otherto afford AA (28.8 g, 61%)

Procedure

A 4.7 M aqueous solution of sodium hydroxide (50 mL) is added into a stirred, ice-cooled solution of ethyl glycinate hydrochloride (32.19 g, 0.23 mole) in water (50 mL). Then, ethyl acrylate (23.1 g, 0.23 mole) is added and the mixture is stirred at room temperature until completion of the reaction is ascertained by TLC. After 19 h the solution is partitioned with dichloromethane (3×100 mL). The organic layer is dried with anhydrous sodium sulfate, filtered and evaporated. The residue is distilled to afford AA (28.8 g, 61%).

Source