Uses
D-Proline Methyl Ester, is a building block used for the synthesis of pharmaceutical compounds, such as Eletriptan (E505000) acting as an Antimigrene.
Synthesis
Thionyl chloride (0.75 mL, 10.43 mmol) was slowly added to a stirred solution of DL-proline (1 g, 8.69 mmol) in methanol (10 mL). The reaction mixture was heated to reflux temperature and stirred continuously for 16 hours. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in dichloromethane (15 mL). Solid sodium bicarbonate was added to quench the excess thionyl chloride, and after filtration, the filtrate was concentrated under reduced pressure to afford methyl (R)-pyrrolidine-2-carboxylate (1.1 g, 98% yield) as a pale yellow solid.
References
[1] Patent: WO2018/20004, 2018, A1. Location in patent: Page/Page column 57
[2] Patent: WO2016/89977, 2016, A1. Location in patent: Paragraph 00143
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5616 - 5624
[4] Chemistry Letters, 1982, p. 745 - 748
[5] Journal of Agricultural and Food Chemistry, 1993, vol. 41, # 9, p. 1458 - 1461
