Pyridine → 3a-methyl-4,5,6,7-tetrahydrobenzo[c]isoxazol-3(3aH)-one

Temperature

65 °C

To a mixture of ethyl 1-methyl-2-oxo-cyclohexanecarboxylate, 37a, (2.05 g, 11.10 mmol) in EtOH (20 mL) was added hydroxylamine hydrochloride (0.97 g, 13.96 mmol) and pyridine (0.99 mL, 12.20 mmol). The mixture was heated to 65° C. overnight. The solution was concentrated in vacuo and the crude material was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc twice more. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (0-35% EtOAc/hexanes) to afford the desired product, 37b.

1. concentrationThe solution was concentrated in vacuo
2. customthe crude material was partitioned between water and EtOAc
3. extractionThe aqueous layer was extracted with EtOAc twice more
4. washThe combined organic phases were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified via silica gel chromatography (0-35% EtOAc/hexanes)

ORD record

ord-24fb37fb2cbc48a5a97a553c9343f4bf

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829007B2