1,8-Diazabicyclo(5.4.0)undec-7-ene → ((1R,4S)-4-azidocyclopent-2-enyl)benzene

Participants

Reaction Steps

A solution of Example 48A (458 mg, 2.86 mmol) and toluene (4.6 mL) was cooled to <5° C. and diphenylphosphoryl azide (0.740 mL, 3.43 mmol) and DBU (0.603 mL, 4.00 mmol) were added. After 5 hours at room temperature, LCMS showed complete reaction. Water (20 mL) and toluene (50 mL) were added and organic layer was washed with water (20 mL), 2N HCl (20 mL), and brine (10 mL) sequentially. The organic layer was dried (Na2SO4), filtered, and concentrated, and crude title compound was used in the next step. MS (DCI) m/z 203 (M+NH4)+.

Provenance & Evidence