1,10-Phenanthroline → HCID 86609638, compound

Participants

Reaction Steps

7-Iodo-5-nitrobenzofuran (2.0 g, 6.9 mmol), tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate* (3.8 g, 17.3 mmol; mixture of cis/trans isomers), 1,10-phenanthroline (0.50 g, 2.8 mmol), CuI (0.26 g, 1.4 mmol) and Cs2CO3 (4.5 g, 13.8 mmol) were heated in toluene (20 mL) at 120° C. for 72 h. The reaction mixture was filtered through Celite and evaporated. The resulting diastereomers were separated by flash chromatography using heptane/EtOAc [(4:1)→(2:1)] to yield 255 mg of the cis-isomer and 919 mg of the trans-isomer. *Prepared according to the procedure described in WO2001085728.

Provenance & Evidence