3-Methoxypropyne → 3-Cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester

Temperatur

70 °C

A solution of 3-cyclopentyl-2-(4-iodo-phenyl)-propionic acid methyl ester (716 mg, 2.0 mmol) and triethylamine (2 mL, 0.01 mmol) in N,N-dimethylformamide (2 mL) was treated with methyl propargyl ether (0.71 mL, 5.0 mmol). The resulting reaction mixture was degassed with argon and then treated with cooper iodide (10 mg, 0.05 mmol) and bis(triphenylphosphine)palladium (II) chloride (15 mg, 0.02 mmol). The reaction was then heated at 70° C. for 24 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. The residue was diluted with ethyl acetate (40 mL) and washed with a half-saturated aqueous sodium chloride solution (1×20 mL). The resulting aqueous layer was back extracted with ethyl acetate (1×40 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 85/15 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-[4-(3-methoxy-prop-1-ynyl)-phenyl]-propionic acid methyl ester (503 mg, 83.8%) as an amber oil: EI-HRMS m/e calcd for C19H24O3 (M+) 300.1725, found 300.1728.

1. customThe resulting reaction mixture
2. customwas degassed with argon
3. temperatureAt this time, the reaction was cooled to 25° C.
4. concentrationconcentrated in vacuo
5. additionThe residue was diluted with ethyl acetate (40 mL)
6. washwashed with a half-saturated aqueous sodium chloride solution (1×20 mL)
7. extractionThe resulting aqueous layer was back extracted with ethyl acetate (1×40 mL)
8. dry with materialThe combined organic extracts were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD-Eintrag

ord-96d0d417010c4e048a0fac7c4cd38ab9

Quelldatensatz

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06388071B2