Cyclohexene → methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate

HRID 465620Notes

Reaction equation

HRID 465620 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][C@H:10]([CH2:17][CH2:18][CH2:19][CH2:20][O:21]CC2C=CC=CC=2)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:2]=1.C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][C@@H:10]([CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 10022866HCID 10022866, compound

Product 1

HCID 10017284methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 4(R)-[3-(3-pyridyl)propyl]-8-(benzyloxy)octanoate (1.67 g, 4.2 mmol) in ethanol (30 ml) is added 20% palladium hydroxide on carbon (0.43 g) followed by cyclohexene (15.6 ml). The mixture is refluxed for 25 hours and then filtered to remove the catalyst. The catalyst is washed with ethanol, the combined filtrate is evaporated, and the residue is purified by flash chromatography on silica gel using 9:1 ethyl acetate/hexane to obtain methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate; IR (CH2Cl2): 3617, 1732, 1197, 1174, 1027 cm- 1.

Workup

  1. temperatureThe mixture is refluxed for 25 hours
  2. filtrationfiltered
  3. customto remove the catalyst
  4. washThe catalyst is washed with ethanol
  5. customthe combined filtrate is evaporated
  6. customthe residue is purified by flash chromatography on silica gel using 9:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0c63ff3714ab416794d346d1f9eaf0a6
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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