Potassium Phosphate, Tribasic → HCID 69119900, compound

Participants

Reaction Steps

To a solution of (5R)-3-[6-(3-buten-1-yloxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (1.00 g) in THF (2 ml) was added a 0.5M solution of 9-borabicyclo[3.3.1]nonane (9-BBN) in THF (6 ml). The solution was stirred at room temperature under nitrogen for 2 h. Tripotassium phosphate (1.05 g) in water (1.5 ml) was added followed by 1-[(1-allylbut-3-enyl)sulfonyl]-3-bromobenzene (0.78 g), palladium acetate (6 mg), and PPh3 (13 mg). The mixture was heated at 600 with vigorous stirring for 22 h. The mixture was allowed to return to room temperature then partitioned between water and EtOAc. The organic phase was washed with brine, dried (MgSO4), and evaporated to dryness. The residual oil was purified on silica SPE bond elut cartridge (50 g) using a gradient of 30%-50% EtOAc in cyclohexane (Gradmaster™). The appropriate fractions were evaporated to give the title compound (1.20 g) LCMS RT=3.91 min.

Provenance & Evidence