Dimethyl Sulfoxide → HCID 86625742, compound

To a solution of DMSO (5.11 mL, 72.1 mmol) in CH2Cl2 (25 mL) at −78° C. was added a solution of oxalyl chloride (3.15 mL, 36.0 mmol) in CH2Cl2 (25 mL) dropwise. After 10 min of additional stirring, a solution of 1-benzyl 2-methyl (2R)-2-(3-hydroxypropyl)pyrrolidine-1,2-dicarboxylate [Cox and Lectka (1998) J. Am. Chem. Soc. 120, 10660-10668] (7.72 g, 24.0 mmol) in CH2Cl2 (50 mL) at −78° C. was added dropwise. After stirring for an additional 1 h, triethylamine (16.7 mL, 120 mmol) was added slowly. The reaction mixture was stirred for 1 h at −78° C. and 2.5 h at ambient temperature. Water (100 mL) was added slowly and the quenched mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were washed with 10% HCl (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-90:10 to 0:100, to give the title compound. MS: m/z=320 (M+1).

1. stirringThe reaction mixture was stirred for 1 h at −78° C. and 2.5 h at ambient temperature
2. extractionthe quenched mixture was extracted with EtOAc (3×100 mL)
3. washThe combined organic extracts were washed with 10% HCl (50 mL) and brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by silica gel chromatography
8. washeluting with a gradient of hexane

ORD record

ord-91b9bee8d373466cb994d025cc6c7c55

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625901B2