Rolipram → HCID 68828335, compound

HRID 1819334Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][NH:18][C:17](=[O:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28][CH3:29])[CH:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>CCOC(C)=O.[Cu]I.O1CCOCC1.CN(C=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][N:18]([C:27]4[CH:26]=[CH:25][C:24]([S:28][CH3:29])=[CH:23][CH:22]=4)[C:17](=[O:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-(3-cyclopentyloxy-4-methoxy-phenyl)-pyrrolidin-2-one (276 mg, 1 mmol), 1-bromo-3-methylsulfanylbenzene (1.4 mmol), K3PO4 (1.5 mmol), DMF (3 mL), dioxane (3 mL) and 1,2-trans-cyclohexanediamine (25 μL) was stirred under N2 for 5 min before CuI (35 mg) was added. The reaction mixture was heated at 110° C. for 20 h under N2 with stirring, then cooled down to r.t. The mixture was diluted with EtOAc, washed with saturated NH4Cl (3×10 mL) and dried over Na2SO4. Concentration and chromatography of the residue on silica gel gave 282 mg of pure product. Yield: 71%.

Workup

additionwas added
temperaturecooled down to r.t
washwashed with saturated NH4Cl (3×10 mL)
dry with materialdried over Na2SO4
concentrationConcentration and chromatography of the residue on silica gel

Sources & evidence

ORD record: ord-88cc2b29803c4a46919d25d6b129e113
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601742B2

Reaction notes

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