Methyl 5-oxo-L-prolinate → HCID 69077734, compound

A portion of (S)-methyl 2-pyrrolidone-5-carboylate (3.00 g, 0.021 mol) was dissolved in DCM (105 mL) and treated with trimethyloxonium tetrafluoroborate (3.10 g, 0.021 mol). The mixture was stirred at room temperature for 24 h. The mixture was concentrated in vacuo. The oil was dissolved in DMF (100 mL). Methyl hydrazinocarboxylate (2.00 g, 0.022 mol) was added and the solution was heated to reflux using a Dean-Stark trap for 24 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography (silica gel, using a gradient of DCM:MeOH 95:5 to 90:10) to provide 3-Oxo-2,5,6,7-tetrahydro-3H-pyrrolo[2,1-c][1,2,4]triazole-5-carboxylic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 4.68-4.72 (m, 1H), 3.82 (s, 3H), 2.75-2.99 (m, 4H); MS (ES+) 184.

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionThe oil was dissolved in DMF (100 mL)
3. temperaturethe solution was heated
4. temperatureto reflux
5. customfor 24 h
6. temperatureThe mixture was cooled to room temperature
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography (silica gel

ORD record

ord-31474d4dbca54e7a814eaa09132f5f05

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618983B2