N-[2-[4-[4-formylphenyl]-3-cyclohexen-1-yl]-propyl] 2-propanesulfonamide → N-[2-[4-(4-cyclopentyl)-3-cyclohexen-1-yl]propyl] 2-propanesulfonamide

HRID 279354

Reaction equation

HRID 279354 reaction equation
[CH:1]([C:3]1C=C[C:6]([C:9]2[CH2:14][CH2:13][CH:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH2:11][CH:10]=2)=[CH:5][CH:4]=1)=O.Br[Zn]C1CCCC1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]1[CH2:1][CH:6]([C:9]2[CH2:14][CH2:13][CH:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:19])=[O:20])[CH2:11][CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 9841299N-[2-[4-[4-formylphenyl]-3-cyclohexen-1-yl]-propyl] 2-propanesulfonamideHCID 178419769HCID 178419769, compound

Product 1

HCID 15541827N-[2-[4-(4-cyclopentyl)-3-cyclohexen-1-yl]propyl] 2-propanesulfonamideYield 45%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Prepared as in Example 14, using 100 mg (0.25 mmol) of the material prepared in step A of Example 13, 1.25 ml of a 0.5 M solution of bromo cyclopentylzinc (0.63 mmol) and 9 mg (0.012 mmol) of bis(triphenylphosphine)palladium chloride in 1 ml of THF. Afforded 35 mg (45%) of the title compound. Ion Electrospray Mass Spectrum: M+1=314.

Workup

  1. customPrepared as in Example 14

Sources & evidence

ORD record
ord-15430aa9e4524157b5005a08db65127e
Source dataset
uspto-grants-2002_03
Patent number
US06362230B1

Linked notes

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