Dimethyl Sulfoxide → HCID 86625742, 화합물

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 기록

ord-f33a0de7589e48efb29aaa0b96dc0fd3

출처 데이터셋

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07893079B2