Methyl iodide → Tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Temperature

25 °C

To a suspension of 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid (500 mg, 2.18 mmol, Astatec Pharmaceutical Technology Co.) in DMF (10 mL) was added methyl iodide (163 μL, 2.62 mmol, Sigma-Aldrich) and K2CO3 (904 mg, 6.53 mmol). These ingredients were stirred at a temperature of about 25° C. for 1 h after which the reaction mixture was quenched with water (20 mL), extracted three times with EtOAc (20 mL for each extraction), washed twice with water (20 mL for each wash), washed with saturated aqueous NaCl (10 mL), dried (MgSO4), and concentrated under reduced pressure to provide tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate as an oil. To a mixture of tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate (2.18 mmol) in dioxane (10 mL) at a temperature of about 25° C. was added 4N HCl in dioxane (10.8 mmol). Then the reaction mixture was stirred at 50° C. for 2 h. Thereafter, the mixture was concentrated under reduced pressure to provide 380 mg of the hydrochloride of methyl 2-(pyrrolidin-3-yl)acetate as a colorless oil (yield 96% for two steps), the identity of which was confirmed using 1H NMR and LC/MS.

1. customwas quenched with water (20 mL)
2. extractionextracted three times with EtOAc (20 mL
3. extractionfor each extraction),
4. washwashed twice with water (20 mL for
5. washeach wash),
6. washwashed with saturated aqueous NaCl (10 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated under reduced pressure

ORD record

ord-76d9db3973124a5dae5fbc58d6a67ebc

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846929B2