Synthesis
1. KOH (42 mg, 0.75 mmol) was added to a methanolic solution of dimethyl cyclopropane-1,1-dicarboxylate (100 mg, 0.63 mmol).
2. The reaction mixture was stirred at room temperature for 4 hours.
3. After completion of the reaction, the solvent was removed by concentration under reduced pressure.
4. The residue was diluted with water and acidified with concentrated hydrochloric acid to pH<2.
5. The acidified aqueous phase was extracted with dichloromethane (3 x 10 mL).
6. The organic phases are combined and dried over anhydrous sodium sulfate.
7. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give cyclopropane-1,1-dicarboxylic acid monomethyl ester (65 mg, 71% yield) as a white solid.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2188 - 2193
[2] Patent: US2009/239848, 2009, A1. Location in patent: Page/Page column 33
[3] Patent: WO2012/74761, 2012, A1. Location in patent: Page/Page column 20-21
[4] Organic Letters, 2011, vol. 13, # 16, p. 4180 - 4183
[5] Patent: EP1577301, 2005, A1. Location in patent: Page/Page column 148
