Ethanol → 4-(3-Benzyl-2-carbamoyl-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 18185

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][C:20]([C:23]#[N:24])=[C:19]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]=3[CH:17]=[C:16]([CH3:32])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1([O-])O[O:34]1.O.O.O.O.[Na+].C(O)C>[Cl-].[Na+].O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:22]3[O:21][C:20]([C:23](=[O:34])[NH2:24])=[C:19]([CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:18]=3[CH:17]=[C:16]([CH3:32])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

4-(3-Benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.302 gm, 0.7 mmol), sodium perborate tetrahydrate (0.43 gm, 2.8 mmol), ethanol (8 ml) and water (8 ml) were combined in a vial and heated in a microwave reactor to 130° C. for 10 minutes. The reaction mixture was cooled to room temperature, diluted with brine and water and extracted three times with ethyl acetate. The solution was dried over magnesium sulfate and purified by column chromatography (methanol/dichloromethane gradient) to give 4-(3-benzyl-2-carbamoyl-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.25 gm, 80% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted three times with ethyl acetate
dry with materialThe solution was dried over magnesium sulfate
custompurified by column chromatography (methanol/dichloromethane gradient)

Sources & evidence

ORD record: ord-6e1cd638c39c4f80be55e1ba89a7d870
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741326B2

Linked notes

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