Ethanol → ethyl (2R)-5-oxopyrrolidine-2-carboxylate

To a solution of (R)-5-oxopyrrolidine-2-carboxylic acid (10 g, 69.84 mmol; available from Aldrich#422614) in EtOH (100 ml) cooled at −5° C., thionyl chloride (10 ml, 139.68 mmol) was added and the resulting mixture was stirred at RT for 3 hrs. Solvents were evaporated in vacuo and the resulting residue was taken up with EtOAc (350 ml), washed with water/TEA (40/12 ml), then with water (40 ml). Collected organics were dried over Na2SO4 and evaporated to afford a residue that was loaded on a SNAP-Si cartridge (50 g) and eluted with a mixture DCM/EtOAc from 90/10 to 50/50. Collected fractions after solvent evaporation afforded a first batch of title compound (D23) (6.4 g). The aqueous were saturated with NaCl and extracted with EtOAc (400 ml). The organic was washed with water (20 ml) dried over Na2SO4 and evaporated in vacuo to afford a second batch of title compound (D23) (3.7 g).

1. customSolvents were evaporated in vacuo
2. washwashed with water/TEA (40/12 ml)
3. dry with materialCollected organics were dried over Na2SO4
4. customevaporated
5. customto afford a residue that
6. washeluted with a mixture DCM/EtOAc from 90/10 to 50/50
7. customCollected fractions after solvent evaporation

ORD record

ord-184e96fdbcb74c6c839564258576c07e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181279B2