Water → HCID 9813358, compound

Temperature

0 °C

((1S,3R)-1-Benzyl-3-methyl-cyclopentylmethyl)-carbamic acid methyl ester (2.6 g, 9.9 mmol) and sodium periodate (29.8 g, 140 mmol) were stirred together in carbon tetrachloride (30 mL), acetonitrile (30 mL), and water for 6 hours. The mixture was cooled to 0° C., and ruthenium(III) chloride (0.04 g, 0.2 mmol) was added to the reaction mixture. The reaction was allowed to warm to room temperature and stirred for 20 hours. Diethyl ether (50 mL) was added, and the mixture was then extracted with saturated aqueous sodium hydrogen carbonate (200 mL). The aqueous layer was acidified to pH 1 with 4N hydrochloric acid and re-extracted with ethyl acetate (200 mL), dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by chromatography (silica gel, eluting with a gradient of heptane to 1:1 heptane:ethyl acetate) to give 0.32 g (14%) of [(1S,3R)-1-(methoxycarbonylamino-methyl)-3-methyl-cyclopentyl]-acetic acid;

1. temperatureto warm to room temperature
2. extractionthe mixture was then extracted with saturated aqueous sodium hydrogen carbonate (200 mL)
3. extractionre-extracted with ethyl acetate (200 mL)
4. dry with materialdried (MgSO4)
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by chromatography (silica gel
7. washeluting with a gradient of heptane to 1:1 heptane

ORD record

ord-7043762af2f84d83bfd7cdaa2e1144a8

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06864390B2