Lithium Hydroxide → HCID 86609851, compound

A mixture of 3-chloro-3-oxopropanoate (0.235 mL, 2.2 mmol), tert-butyl 3-aminopyrrolidine-1-carboxylate (410 mg, 2.2 mmol), DCM (4.4 mL) and DIPEA (0.766 mL, 4.4 mmol) was stirred for 2 h at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was re-dissolved in THF (2.2 mL), treated with LiOH×H2O (0.185 g, 4.4 mmol) in water (2.2 mL) for 2 h at room temperature and concentrated under reduced pressure to remove the THF. The remaining aqueous solution was extracted with EtOAc, acidified with 2N HCl (until pH˜5), extracted again with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound 35 (286 mg, 48% yield) as a light brown foam which was used in the next step without further purification. MS (m/z): 273.1 (M+H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was re-dissolved in THF (2.2 mL)
3. concentrationconcentrated under reduced pressure
4. customto remove the THF
5. extractionThe remaining aqueous solution was extracted with EtOAc
6. extractionextracted again with EtOAc
7. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-096cbf5b8f2b4fdb91d63ff3bd81a476

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093264B2