Triphenylphosphine → (1S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopent-2-enol

Participants

Reaction Steps

(2-Chloro-9H-purin-6-yl)-(2,2-diphenyl-ethyl)-amine (12.92 g, 36.97 mmol) is placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (100 ml) and dry DMSO (2 ml) are added and the suspension is cooled on an ice-bath. Sodium hydride 95% (0.89 g, 36.97 mmol) is then slowly added and the solution is stirred at room temperature for 30 minutes. (1S,4R)-cis 4-Acetoxy-2-cyclopenten-1-ol (5.00 g. 35.20 mmol) and triphenylphosphine (1.38 g, 5.28 mmol) are placed in an oven-dried flask under an atmosphere of argon. Dry deoxygenated THF (50 ml) is added. This solution is added to the anion solution. Tetrakis(triphenylphosphine)palladium(0) (2.03 g, 1.76 mmol) is added and the reaction mixture is stirred at 50° C. The reaction is shown to be complete by LCMS after 3 hours. The reaction mixture is allowed to cool and the solvent is removed in vacuo. The residue is taken up in dichloromethane (50 ml) and poured into vigorously stirring diethyl ether (300 ml). The precipitate is filtered off, the filtrate is taken and the solvent is removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 7.65(m, 1H), 7.35-7.15(m, 10H), 6.35(m, 1H), 5.90(m, 1H), 5.80(m, 1H), 5.50(m, 1H), 5.25(d, 1H), 4.85(t, 1H), 4.35(t, 1H), 4.25(m, 2H), 2.95(m, 1H), 2.15(d, 1H), MS (ES+) m/e 432 (MH+).

Provenance & Evidence