Tri-o-tolylphosphine → Tert-butyl 2,6-dichlorophenethyl(3-(2-oxopropyl)benzyl)carbamate

Participants

Reaction Conditions

Reaction Steps

[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-carbamic acid tert-butyl ester (Example 14, step b) (500 mg), tributyltin methoxide (350 μL), isoprenyl acetate (170 μL), tri-o-tolylphosphine (30 mg) and toluene (20 mL) were charged to a flask and the solution degassed with nitrogen for 5 minutes. Palladium acetate (10 mg) was added and the resultant mixture heated to 100° C., under nitrogen, for 3 hours. On cooling, potassium fluoride (580 mg) in water (3 mL) was added, stir at room temperature for 18 hours. The solids were filtered off, and the filter cake washed with ethyl acetate. The filtrate was evaporated and purified on silica, eluting with a gradient of iso-hexane/ethyl acetate [4:1 to 2:1], to give the subtitle product as an oil (230 mg).

Provenance & Evidence