Ethyl 3-(2-propanyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate → HCID 20035410, compound

HRID 1905356Notes

Reaction equation

HRID 1905356 reaction equation
[CH:1]([CH:4]1[CH:9]2[CH2:10][CH:6]([CH:7]=[CH:8]2)[CH:5]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:3])[CH3:2]>[Pd].C(O)C>[CH:1]([CH:4]1[CH:9]2[CH2:10][CH:6]([CH2:7][CH2:8]2)[CH:5]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15904484Ethyl 3-(2-propanyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

Product 1

HCID 20035410HCID 20035410, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.35 g of 5% palladium on charcoal as catalyst was added to 6.5 g of ethyl 3-isopropyl-5-bicycloheptene-2-carboxylate (mixture of isomers obtained according to Example 5) dissolved in 30 ml of ethanol, after which the mixture was hydrogenated at 20° C. for 1 hour under a hydrogen pressure of 100 kPa. The catalyst was then filtered off, the filtrate evaporated down and the evaporation residue distilled. 5.7 g were obtained of the desired compound as a mixture of endo- and exo-isomer. b.p.: 89° C./0.7 kPa; NMR (of the mixture): 0.7-1.0 (6H); 1.2 (3H, t); 1.0-2.5 (11H); 3.9-4.2 (2H).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate evaporated down
  3. distillationthe evaporation residue distilled

Sources & evidence

ORD record
ord-0941118b50b042cfbd439388450170d8
Source dataset
uspto-grants-1989_06
Patent number
US04843061

Reaction notes

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