Cyclohexene → Methyl 4-[(1-hydroxy-2-methylindolizin-3-yl)carbonyl]benzoate

HRID 1716352Notes

Reaction equation

HRID 1716352 reaction equation
C1CCCCC=1.C([O:14][C:15]1[C:16]([CH3:36])=[C:17]([C:24]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[O:25])[N:18]2[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]2)C1C=CC=CC=1>C(O)C.[Pd]>[OH:14][C:15]1[C:16]([CH3:36])=[C:17]([C:24]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[O:25])[N:18]2[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]2

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 12069558Methyl 4-[(1-(benzyloxy)-2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 12069595Methyl 4-[(1-hydroxy-2-methylindolizin-3-yl)carbonyl]benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8.75 ml (86.37 mmol) of cyclohexene are added to 3.45 g (8.64 mmol) of methyl 4-[(1-(benzyloxy)-2-methylindolizin-3-yl)carbonyl]benzoate in 40 ml of ethanol, in the presence of 690 mg of 10% Pd/C, and the medium is heated under reflux for one hour.

Workup

  1. temperaturethe medium is heated
  2. temperatureunder reflux for one hour

Sources & evidence

ORD record
ord-411c6c6c60b14d68bf58a0ec50278fab
Source dataset
uspto-grants-2010_09
Patent number
US07803811B2

Reaction notes

Loading…