Sodium hydride → tert-Butyl [3-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-3-benzazepin-3-yl)propyl]-methylcarbamate

HRID 420861

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

Suspend 1.7 g (7.8 mmol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one in 35 ml of DMF and then add 374 mg (9.35 mmol, 1.2 equivalents) of sodium hydride (60% suspension in oil). A clear pale yellow solution is obtained, which is stirred for one hour at 25° C. 1.94 g (9.35 mmol, 1.2 equivalent) of tert-butyl (3-chloropropyl)methylcarbamate dissolved in 10 ml of DMF are then added dropwise. The whole is heated at 50° C. overnight and then the solvent is evaporated to dryness. The residue is taken up in water and extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 4.2 g of an oil is obtained which is purified by flash chromatography on 200 g of silica (eluant=dichloromethane/ethyl acetate:80/20). 2.3 g of the expected product are obtained in the form of a colourless oil.

Aufarbeitung

customA clear pale yellow solution is obtained
additionare then added dropwise
temperatureThe whole is heated at 50° C. overnight
customthe solvent is evaporated to dryness
extractionextracted with dichloromethane
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-42615ccfe9fc46af87de3f803fcdde36
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08097720B2

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