methyl D-prolinate Chemical Properties

Boiling point:

169.9±33.0 °C(Predicted)

Density 

1.055±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

8.23±0.10(Predicted)

methyl D-prolinate Usage And Synthesis

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

methyl D-prolinate (43041-12-9)Related Product Information

• D-Prolinamide
• 1,3-Adamantanediol
• cis-cyclo(Pro-Pro)
• Cyanuric acid
• 3-Amino-1-hydroxyadamantane
• Vildagliptin iMpurity A-F
• Vildagliptin Carboxylic Acid
• 2-Pyrrolidinecarboxamide,1-(hydroxyacetyl)-,(S)-(9CI)
• L-Proline, 4-chloro-, trans-
• 1,3,5,7-tetrahydroxyadamantane
• Amantadine
• Vildagliptin Impurity 19
• N-acetic acid-1-aMino-3-adaMantanol
• Vildagliptin IMpurity 2 (Mixture of DiastereoMers)
• 1-Adamantanol
• Vildagliptin Impurity 6
• Vildagliptin Impurity 25
• Dichloroacetyl chloride