Ethanol → 4-(2-Fluoropyridin-3-yl)cyclohexanol

HRID 410237Notes

Reaction equation

HRID 410237 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(O)C>[Pd].O1CCCC1>[F:1][C:2]1[C:7]([CH:8]2[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 593267944-(2-Fluoropyridin-3-YL)cyclohex-3-enol

Product 1

HCID 585477094-(2-Fluoropyridin-3-yl)cyclohexanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a flask containing 4-(2-fluoropyridin-3-yl)cyclohex-3-enol (750 mg, 3.88 mmol) and Ethanol (31.100 ml):Tetrahydrofuran (7.78 ml) was added 10% palladium on carbon, (240 mg, 2.255 mmol) before purging the reaction of air and backfilling with hydrogen. It was stirred for 3 h at room temperature before adding an additional 30 mol % Pd/C and stirring at 40° C. for 16 h. The reaction mixture was cooled and filtered through Celite before concentrating under reduced pressure to yield 4-(2-fluoropyridin-3-yl)cyclohexanol as a pale yellow oil that was used without purification. MS (ESI, pos. ion) m/z: 196.1 (M+1).

Workup

  1. custombefore purging
  2. customthe reaction of air and backfilling with hydrogen
  3. stirringstirring at 40° C. for 16 h
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered through Celite
  6. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-11fcbd2b58ca41f4a25218635d5488b1
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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