3-(2-Fluoropyridin-3-yl)cyclohex-2-enone → (Rac)-trans-3-(2-fluoropyridin-3-yl)cyclohexanol

HRID 1880122

Reaktionsgleichung

[F:1][C:2]1[C:7]([C:8]2[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>C1COCC1>[F:1][C:2]1[C:7]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([OH:14])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

A mixture of 3-(2-fluoropyridin-3-yl)cyclohex-2-enone (1100 mg, 5.75 mmol) and 1,1′-bis(di-1-propylphosphino)ferrocene(1,5-cyclooctadiene)rhodium (i) tetrafluoroborate (412 mg, 0.575 mmol) in THF (40 mL) was stirred at 45° C. under an atmosphere of hydrogen gas for 5 h. The mixture was filtered through a Celite pad that was washed with THF. Concentration of the combined filtrated and washings under reduced pressure, followed by flash chromatography on silica gel (0% to 50% EtOAc in hexanes) afforded (rac)-trans-3-(2-fluoropyridin-3-yl)cyclohexanol as a colorless oil together with its cis-isomer. MS (ESI, pos. ion) m/z: 196.1 (M+1). IC50 (uM) +++++.

Aufarbeitung

filtrationThe mixture was filtered through a Celite pad that
washwas washed with THF
filtrationConcentration of the combined filtrated

Quellen und Nachweise

ORD-Eintrag: ord-27060d31709445dfa95b61e336b67b8a
Quelldatensatz: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08318718B2

Verknüpfte Notizen

Wird geladen…