tert-Butyl hydroperoxide → N-Cyclopropyl-3-propyloxirane-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A flask equipped with a stir bar, thermometer and addition funnel was placed under a nitrogen atmosphere then charged with samarium (III) isopropoxide (Sm(O-i-Pr)3, 430 mg, 1.3 mmol), triphenyl arsine oxide (Ph3As═O; 420 mg, 1.3 mmol), S-(−)1,1′-bi-2-naphthol ((S)-BINOL), 370 mg, 1.3 mmol), 4 Å molecular sieves (13 g) and THF (20 mL) then stirred for 30 min at 25±5° C. Tert-butyl hydroperoxide (2.8 mL, 5.5 M, 16 mmol) was then added. The mixture stirred for 30 minutes at 25±5° C., the amide of Example 4 (2.0 g, 13 mmol) in THF (2.0 mL) was then added. The reaction was stirred for 14 hours after which time the reaction had reached 95% completion as determined by HPLC.

Provenance & Evidence