3-(2-Fluoropyridin-3-YL)cyclopent-2-enol → HCID 59327186, compound

HRID 1880168Notes

Reaction equation

HRID 1880168 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>O1CCCC1.[Pd]>[F:1][C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 593271673-(2-Fluoropyridin-3-YL)cyclopent-2-enol

Product 1

HCID 59327186HCID 59327186, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 3-(2-fluoropyridin-3-yl)cyclopent-2-enol (1184 mg, 6.61 mmol) in tetrahydrofuran (40 mL) was treated with palladium, 10% wt. on activated carbon (703 mg, 0.661 mmol). The reaction mixture was evacuated under vacuum and backfilled with hydrogen (3×), and stirred under hydrogen at 23° C. After 4 h, the reaction was filtered through celite, the filter cake washed with 1:1 methanol:dichloromethane (50 mL), the filtrates combined and concentrated, affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 182.0 (M+1).

Workup

  1. customThe reaction mixture was evacuated under vacuum
  2. filtrationthe reaction was filtered through celite
  3. washthe filter cake washed with 1:1 methanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2378858e52bd45669da0d49813836db0
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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