Quinoline → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylate

HRID 1639426Notes

Reaction equation

HRID 1639426 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 13093787Tert.-butyl(1R,cis)2,2-dimethyl-3-(carboxy ethynyl)cyclopropane-carboxylate

Product 1

HCID 12807775tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2 g of 1,1-dimethylethyl (1R,cis) 2,2-dimethyl-3[2-carboxyethynyl]-cyclopropane-carboxylate in 41 ml of ethyl acetate were hydrogenated in the presence of 0.38 g of 10% palladium hydroxide on barium sulfate and 0.4 ml of quinoline and the mixture was filtered. The filtrate was washed with 0.5N hydrochloric acid, then with water until neutral, dried and evaporated to dryness under reduced pressure to obtain 2 g of 1,1-dimethylethyl (1R,cis) 2,2-dimethyl-3-[(Z) 2-carboxyethenyl]-cyclopropane-carboxylate melting at 94° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with 0.5N hydrochloric acid
  3. dry with materialwith water until neutral, dried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-db4300890d0a4e80b7231e476af9bdba
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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