Dimethyl Sulfoxide → HCID 86760351, compound

Temperature

0 °C

In methylene chloride (43 ml) were dissolved 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propanol (2.84 g, 9.30 mmol), triethylamine (7.78 ml, 55.8 mmol) and DMSO (6.61 ml, 93.7 mmol). Under stirring at 0° C., a pyridine-sulfur trioxide complex (4.44 g, 27.9 mmol) was added dropwise to the resulting solution. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Water (50 ml) was added to the residue obtained by distilling off the solvent under reduced pressure, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby hexane/ethyl acetate (4/1) eluate fractions, the title compound (1.35 g, 53%) was obtained as a colorless oil.

1. additiona pyridine-sulfur trioxide complex (4.44 g, 27.9 mmol) was added dropwise to the resulting solution
2. additionAfter completion of the dropwise addition
3. stirringthe reaction mixture was stirred at room temperature for 2 hours
4. customobtained
5. distillationby distilling off the solvent under reduced pressure
6. extractionfollowed by extraction with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. distillationdistilled under reduced pressure
10. customto remove the solvent
11. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby hexane/ethyl acetate (4/1) eluate fractions

ORD record

ord-21a2b234b2554b2e88a9101802c9202b

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2