(2S,4S)-tert-butyl-4-(diphenylphosphino)-2-(diphenylphosphino)-2-(diphenylphosphinomethyl)-1-pyrrolidinecarboxylate → (S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid

참여 물질

반응 단계

(E)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt (100 mg, 0.22 mmole), chloro(1,5-cyclooctadiene)rhodium(I)dimer (3.0 mg, 0.0006 mmole) and (2S,4S)-tert-butyl-4-(diphenylphosphino)-2-(diphenylphosphino)-2-(diphenylphosphinomethyl)-1-pyrrolidinecarboxylate (7.6 mg, 0.013 mmole) were charged to a glass vial and the top sealed with a rubber septum. The system was purged with argon, methanol (2.5 mL) was added and the mixture purged with argon for 30 minutes. The reaction was hydrogenated at 104 kPa (15 p.s.i.) and room temperature for 20.5 hours. The reaction mixture was purged with nitrogen, Dowex 50W-X2 ion exchange resin (200 mesh, 100 mg) added and the mixture stirred for 15 minutes. The ion exchange resin was removed by filtration and the methanol removed by evaporation under reduced pressure to give the title compound as an oil (73 mg, quantitative) (ratio S:R 61:39), Rf =0.3 (ethyl acetate/hexane, 1:1+1% acetic acid).

출처 및 근거