Triphenylphosphine → HCID 86629375, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (2.6 mL, 13 mmol) was added in drops to a mixture of 3-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (2.6 g, 10 mmol), 1-oxaspiro[4.5]decan-8-ol (U.S. Pat. No. 4,438,130, Mar. 20, 1984, 1.6 g, 11 mmol), and triphenylphosphine (2.9 g, 11 mmol) in tetrahydrofuran (80 mL). After stirring at room temperature, the mixture was purified by reverse phase high performance liquid chromatography on a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 15% acetonitrile/85% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile to provide two separable diastereomers of 3-(6-chloro-1-(1-oxaspiro[4.5]decan-8-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 404.2 (M+H)+

Provenance & Evidence