Quinoline → HCID 13188398, compound

HRID 464464Notes

Reaction equation

HRID 464464 reaction equation
[CH3:1][C:2]1([CH3:34])[C@@H:4]([C:5]#[C:6][C:7]([O:9][C:10]([CH2:13][CH3:14])([CH3:12])[CH3:11])=[O:8])[C@H:3]1[C:15]([O:17][C@H:18]([C:32]#[N:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].N1C2C(=CC=CC=2)C=CC=1>[OH-].[Pd+2].[OH-].C(OCC)(=O)C>[CH3:34][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][C:10]([CH2:13][CH3:14])([CH3:11])[CH3:12])=[O:8])[C@H:3]1[C:15]([O:17][C@H:18]([C:32]#[N:33])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:16]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 56978820HCID 56978820, compound

Product 1

HCID 13188398HCID 13188398, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.34 g of the product of Step A, 220 mg of 10% palladium hydroxide on barium sulfate, 20 ml of ethyl acetate and 0.25 ml of quinoline was hydrogenated for 30 minutes and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 9:1 cyclohexane-ethyl acetate mixture yielded 1.05 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(tert.-amyloxycarbonyl)-ethenyl]cyclopropane-carboxylate with a specific rotation of [α]D20 =+63.5°±2.5° (c=0.7% in chloroform).

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. washElution with a 9:1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-f980e91c903240dea9d8f10ac95a964c
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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