Bromide ion → Isohexane ethyl acetate

Participants

Reaction Steps

A mixture of the bromide from Step 3 (0.075 g), the homochiral boronate ester from Example 24, Step 1 (0.105 g), tetrakis(triphenylphosphine) palladium (0) (0.1 g), 2M aqueous sodium carbonate (0.22 mL) and toluene (3 mL) was refluxed for 4 hours. The mixture was cooled, diluted with ethyl acetate (15 mL) and washed with water (10 ml). The organic phase was filtered through a Teflon membrane and concentrated. Flash column chromatography, eluting with 20% then 30% then 50% ethyl acetate-isohexane, gave the product as a yellow oil (0.085 g, 63%). MS (ES+) 628 ([MH]+). Step 5: [6S,9R,11R] 2′,3′,4′,5,5′,6,7,8,9,10-Decahydro-2-(4-(4-fluorophenyl)-1H-imadazol-2-yl)-5′-(2,2,2-trifluoroethyl)-spiro[6,9-methanobenzocyclooctene-11,3′-[1,2,5]thiadiazole] 1′,1′-dioxide.

Provenance & Evidence