N,N,N-Tributylbutan-1-aminium trifluoroacetate → 4-[3-(3-Hydroxy-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]benzonitrile

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Reaction Steps

17 g of 4-[3-(3-bromo-3-phenylpropyl)-2-(4-methoxyphenyl)-4-oxoazetidin-1-yl]-benzonitrile are dissolved in 500 ml of dioxane and, after addition of 34 ml of ˜40 percent tetrabutylammonium trifluoroacetate solution, heated to reflux for 24 h. The mixture was concentrated to about half the volume, mixed with water and methyl tert-butyl ether and separated into the phases. The organic phase is concentrated, and the residue is stirred with 500 ml of ethanol and 200 ml of concentrated ammonia at room temp. for 1 h. It is then again concentrated in vacuo, and the crude product is purified on silica gel with dichloromethane/methanol =30:1 as mobile phase. The alcohol is obtained as an oil. MS (ESI): 413 (M+H+), 395 (M+H+-H2O) [C26H24N2O3 M=412].

Provenance & Evidence