Sodium hydride → HCID 67405296, compound

Temperature

0 °C

Trimethyl phosphonoacetate (0.95 ml, 5.88 mmol) was dissolved in THF (40 ml). Under a nitrogen gas stream, sodium hydride (60% in oil, 235 mg, 5.88 mmol) was added in portions to the resulting solution, while stirring at 0° C. After stirring the reaction mixture at the same temperature for 10 minutes, a solution of 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propionaldehyde (1.35 g, 4.90 mmol) in THF (40 ml) was added dropwise at 0° C. The reaction mixture was further stirred for 2 hours at 0° C. and poured in ice water (50 ml), 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 from chloroform/acetone (10/1) eluate fractions, the title compound (1.40 g, 86%) was obtained as a colorless oil.

1. stirringAfter stirring the reaction mixture at the same temperature for 10 minutes
2. stirringThe reaction mixture was further stirred for 2 hours at 0° C.
3. extractionfollowed by extraction with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent
8. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/acetone (10/1) eluate fractions

ORD record

ord-fcd66166ef7c44eaab1a5d171a3aff61

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2