Acetic Acid → HCID 86681844, compound

A methanol (9 mL) solution of (±)-2-methyl-2H-pyran-3(6H)-one (370 mg, 3.30 mmol) was treated with a suspension of 10% palladium on carbon (185 mg) in methanol (3 mL). The mixture was sparged under hydrogen and stirred for 45 minutes at ambient temperature. The mixture was sparged under nitrogen, treated with tert-butyl carbazate (436 mg, 3.30 mmol, 1 equiv) and acetic acid (0.756 mL, 13.2 mmol, 4 equiv) and sparged under hydrogen. After stirring for 1 hour, the mixture was sparged under nitrogen and filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with sodium bicarbonate (30 mL, saturated aqueous) and the organic extract was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate) to provide the titled compound.

1. customThe mixture was sparged under hydrogen
2. customThe mixture was sparged under nitrogen
3. customsparged under hydrogen
4. stirringAfter stirring for 1 hour
5. customthe mixture was sparged under nitrogen
6. filtrationfiltered through a pad of celite
7. concentrationThe filtrate was concentrated in vacuo
8. dissolutionthe residue was dissolved in ethyl acetate
9. washwashed with sodium bicarbonate (30 mL, saturated aqueous)
10. extractionthe organic extract
11. dry with materialwas dried with sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate)

ORD record

ord-a6a240f5d66a44c48a54e931075662b5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653079B2