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

HRID 1995150Notes

Reaction equation

HRID 1995150 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 12807746tert.-butyl(1R,cis)2,2-dimethyl-3-[2-(methoxy carbonyl)-ethynyl]-cyclopropane-carboxylate

Product 1

HCID 13253938tert.-butyl(1R,cis)2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane carboxylateYield 90.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

12 g of the product of Step A in 240 cm3 of ethyl acetate were hydrogenated in the presence of 2.4 g of 10% palladium hydroxide on barium sulfate and 2.4 cm3 of quinoline. The mixture was filtered and the filtrate was evaporated to dryness to obtain 11 g of tert.-butyl (1R,cis) 2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane carboxylate.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-aa1541f8e0b946518528ef72d05371ad
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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