1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18433602, compound

Participants

Reaction Steps

To a stirred solution of (3-benzyloxyphenyl)(3-chlorophenyl)methanol, as described above in Step A, (4.0 g, 12.3 mmol) and diphenylphosphoryl azide (4.1 g, 14.9 mmol) in dry toluene (35 mL) at 0° C., was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.1 g, 13.8 mmol). The resulting mixture was allowed to warm to ambient temperature, and stirred under argon for 18 hours, then washed with 5% hydrochloric acid (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—2% EtOAc to yield the product as a colorless oil.

Provenance & Evidence