Acetic Acid → HCID 69828048, compound

Temperature

20 °C

To a solution of (3aR,4S,6R,6aR)-N-(2-hydroxybutyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole4-carboxamide (3.81 g) in anhydrous dichloromethane (115 ml), containing powdered 4 Å molecular sieves (5.7 g) at 0° C., under nitrogen, were added acetic acid (2.59 ml) and potassium dichromate (7.93 g), portionwise. The reaction mixture was stirred at 0° C. for 15 min and at 20° C. for a further 2 h. The mixture was quenched with isopropanol (40 ml) and stirred for 30 min, silica gel (Merck 9385) (40 g) and ethyl acetate (100 ml) were added, and the mixture was stirred for a further 30 min. This mixture was filtered through ‘harborlite®’ filter aid and the filtrate concentrated in vacuo to give a crude product which was purified by flash column chromatography on silica gel, eluting with 2:1 ethyl acetate:cyclohexane to give the title compound (1.91 g)

1. customThe mixture was quenched with isopropanol (40 ml)
2. stirringstirred for 30 min
3. additionsilica gel (Merck 9385) (40 g) and ethyl acetate (100 ml) were added
4. stirringthe mixture was stirred for a further 30 min
5. filtrationThis mixture was filtered through ‘harborlite®’
6. filtrationfilter aid
7. concentrationthe filtrate concentrated in vacuo
8. customto give a crude product which
9. customwas purified by flash column chromatography on silica gel
10. washeluting with 2:1 ethyl acetate

ORD record

ord-c557665df6fe48549d23d955f26310f0

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492348B1