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

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.

1. additionTo the stirred solution was added
2. stirringThe reaction mixture was stirred until analysis by GC
3. customless than 1% (approximately 2 h)
4. filtrationThe reaction mixture was filtered
5. washthe wet cake (excess K2CO3) was washed with CH3CN (5-10 mL)
6. concentrationThe filtered solution was then concentrated under reduced pressure to minimum volume (white slurry)
7. additionMethyl t-butyl ether (MTBE) and H2O were added, at which time all solids
8. dissolutiondissolved
9. washThe organic layer was washed a second time with water
10. concentrationconcentrated

ORD record

ord-b708c59ba43e409ebfe1c0f12dcdf97c

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106088B2