Reaktion #10510

Reaktionsgleichung

2-(R)-methylpyrrolidine HCl

K2CO3

Ethyl acrylate

EtOH

ethyl acrylate

→

title compound

Ausbeute 100.8%

3-(2-(R)-Methyl-pyrrolidin-1-yl)-propionic acid ethyl ester

Ausbeute 100.8%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo the stirred solution was added
2. 2
   workup.STIRRINGThe reaction mixture was stirred until analysis by GC
3. 3
   Sonstigeless than 1% (approximately 2 h)
4. 4
   FiltrationThe reaction mixture was filtered
5. 5
   Waschenthe wet cake (excess K2CO3) was washed with CH3CN (5–10 mL)
6. 6
   EinengenThe filtered solution was then concentrated under reduced pressure to minimum volume (white slurry)
7. 7
   workup.ADDITIONMethyl t-butyl ether (MTBE) and H2O were added, at which time all solids
8. 8
   workup.DISSOLUTIONdissolved
9. 9
   WaschenThe organic layer was washed a second time with water
10. 10
    Einengenconcentrated

Vorschrift

In a round-bottom flask, 2-(R)-methylpyrrolidine HCl (5.5 g, 45 mmol) was dissolved in CH3CN (20 mL). To the stirred solution was added milled K2CO3 (8.3 g, 60 mmol). The suspension was stirred at room temperature for approximately 1 h. Ethyl acrylate (3.25 mL, 30 mmol) and EtOH (40 mL) were then added. The reaction mixture was stirred until analysis by GC showed completion (the Area % of ethyl acrylate was less than 1% (approximately 2 h)). The reaction mixture was filtered and the wet cake (excess K2CO3) was washed with CH3CN (5–10 mL). The filtered solution was then concentrated under reduced pressure to minimum volume (white slurry). Methyl t-butyl ether (MTBE) and H2O were added, at which time all solids dissolved. The organic layer was washed a second time with water and then concentrated to yield 5.6 g of the title compound. The oil product was used in the next step without further purification.

Quelle