Tetrahydrofuran → HCID 86760758, compound

Participants

Reaction Steps

A stirred mixture of 10 g of racemic trans [3-(2-bromo-3-phenyl-allyloxy)-cyclopentyl]-carbamic acid benzyl ester, 4.7 g of p-tolylboronic acid, 160 mg of o-biphenyl dicyclohexylphosphine, 52 mg of palladium acetate, 4 g of potassium fluoride and 25 mL of anhydrous tetrahydrofuran was stirred at room temperature for 1 h then heated to 50° C. for 3h under nitrogen atmosphere. The mixture was cooled diluted with 50 mL of sodium carbonate and extracted with 3×100 mL portions of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of 0% to 25% ethyl acetate in hexane gave 10.8 g of product as a crystalline solid: MS (m+1)=442.3; 1H NMR (400 MHz, CDCl3) 7.35 (m, 4H), 7.1 (m, 8H), 7.0 (d, 2H), 6.6 (s, 1H), 5.1 (s, 2H), 4.7 (br s, 1H), 4.2 (s, 2H), 4.1 (m, 1H), 2.37 (s, 3H), 2.2 (m, 2H), 1.986 (m, 1H), 1.78 (m, 1H), 1.62 (m, 1H), 1.4 (m, 1H).

Provenance & Evidence