Sodium hydride → (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-(pentan-3-yl)piperidin-2-one

To a suspension of 1.81 g (4.8 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (Example 71, Step D) in 3-bromopentane (17.6 mL) added 967 mg (60 wt. % in mineral oil, 24.2 mmol) of sodium hydride. The resulting milky white slurry was heated at 120° C. for 20 h, and then more 3-bromopentane (5.1 mL) was added. After an additional 24 h at 120° C., the reaction was cooled to room temperature and quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3×) and the combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2 to 26% EtOAc/hexanes, gradient elution) provided the title compound as a white solid.

1. temperaturethe reaction was cooled to room temperature
2. customquenched with saturated aqueous ammonium chloride
3. extractionThe mixture was extracted with ethyl acetate (3×)
4. dry with materialthe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. customPurification of the residue by flash chromatography on silica gel (2 to 26% EtOAc/hexanes, gradient elution)

ORD-Eintrag

ord-9c69a4b3dff84c99a7ab3763bd410706

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08569341B2