Triphenylphosphine → HCID 17797592, compound

Participants

Reaction Steps

To a round bottom flask was added 6-bromo-1,3-benzothiazol-2(3H)-one (0.300 g, 1.304 mmol), tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.365 g, 1.695 mmol), triphenylphosphine (0.455 g, 1.695 mmol), diisopropyl (E)-diazene-1,2-dicarboxylate (DIAD) (0.330 mL, 1.695 mmol), and NMP (5 mL). The reaction mixture was then permitted to stir at room temperature for two hours. The crude reaction mixture was then diluted with methanol, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 30% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) tert-butyl 4-[(6-bromo-2-oxo-1,3-benzothiazol-3(2H)-yl)methyl]piperidine-1-carboxylate (11-1) as a tan solid. HRMS (M+H)+: observed=427.0691, calculated=427.0686.

Provenance & Evidence