(1S,4S)-4-(3-pyridyl)-2-cyclopenten-1-ol → (1R,3R)-3-(3-pyridyl)cyclopentanol

HRID 655162

Reaction equation

HRID 655162 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@H:7]2[CH2:11][C@H:10]([OH:12])[CH:9]=[CH:8]2)[CH:2]=1>CCO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:8][CH2:9][C@@H:10]([OH:12])[CH2:11]2)[CH:2]=1

Participants

4

Reactant 1

HCID 59486121(1S,4S)-4-(3-pyridyl)-2-cyclopenten-1-ol

Product 1

HCID 59486143(1R,3R)-3-(3-pyridyl)cyclopentanolYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1S,4S)-4-(3-pyridyl)-2-cyclopenten-1-ol (1.86 g, 11.5 mmol) and 10% Pd/C (186 mg) in EtOH (35 mL) was stirred under hydrogen atmosphere for 3 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. (1R,3R)-3-(3-pyridyl)cyclopentanol (1.82 g, 97%) was yield as yellow oil.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f2d094fcfd834f89a25ee48b8793f655
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Linked notes

Loading…