Triphenylphosphine → tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Participants

Reaction Steps

Diisopropyl azodicarboxylate (0.71 mL, 3.6 mmol) was added in drops to a suspension of 3-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (0.53 g, 2.0 mmol), tert-butyl 4-hydroxy-1-piperidinecarboxylate (0.48 g, 2.4 mmol), and triphenylphosphine (0.79 g, 3.0 mmol) in tetrahydrofuran (20 mL). After stirring at room temperature for 16 hours, the mixture was adsorbed onto flash silica gel and purified by automated flash chromatography (hexanes/ethyl acetate) to provide tert-butyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate as a white solid contaminated with a light yellow material (0.81 g, 90%). MS (ES+): 448.9, 450.2 (M+H)+

Provenance & Evidence