Ethanol → 4,4'-(1-(4-(6-(Dimethylamino)pyridin-3-yl)phenyl)pyrrolidine-2,5-diyl)dianiline

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Reaction Steps

The product from Example 99A (26.8 mg, 0.053 mmole) was dissolved in THF (526A) in a round bottom flask to which was subsequently added ethanol (526 μL) resulting in a yellow precipitate. To this suspension was added platinum (IV) oxide (3.16 mg, 0.014 mmole). The flask was capped with a septum and the contents vacuum degassed three times. Hydrogen was introduced via a balloon and the mixture allowed to stir at room temperature for two and one half hours. The reaction mixture was vacuum filtered through a sand and celite plug, which was rinsed with THF and methanol until the filtrate was u.v.(−). The filtrate was concentrated in vacuo to provide the title compound in quantitative yield as a white solid as a mixture of stereoisomers. MS ESI(+), m/z @ 450.7 (M+H)+.

Provenance & Evidence