Potassium Carbonate → 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

To a solution of 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one (1.12 g, 4.731 mmol) in ethanol (15 mL) was added potassium carbonate (1.962 g, 14.19 mmol) and methoxyamine hydrochloride (494 mg, 5.914 mmol). The reaction mixture was heated at reflux for 12 h. Upon cooling to room temperature, the reaction mixture was filtered, and the white solids were washed with diethyl ether. The filtrate was concentrated in vacuo, and the residue was partitioned between diethyl ether and water. The product was extracted with diethyl ether (2×30 mL). The organic layers were washed with brine and dried over anhydrous sodium sulfate. The solids were then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 1–2% ethyl acetate in hexanes yielded 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (762 mg, 61%) as clear oil.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 12 h
3. filtrationthe reaction mixture was filtered
4. washthe white solids were washed with diethyl ether
5. concentrationThe filtrate was concentrated in vacuo
6. customthe residue was partitioned between diethyl ether and water
7. extractionThe product was extracted with diethyl ether (2×30 mL)
8. washThe organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationThe solids were then filtered off
11. concentrationthe filtrate was concentrated in vacuo
12. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
13. washeluting with 1–2% ethyl acetate in hexanes

ORD-Eintrag

ord-7234d026b3de446a97f57d6a7cf6a50a

Quelldatensatz

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07132421B2