Trimethylphosphine → HCID 58460146, compound

Participants

Reaction Steps

To a suspension of Intermediate 34 (300 mg) and triethylmethanetricarboxylate (0.417 ml) in toluene (3.5 ml) and methyltetrahydrofuran (3.50 ml), stirred at RT under an inert atmosphere of nitrogen, was added trimethylphosphine, 1M in toluene (1.97 ml). The resulting solution was cooled to −78° C. and diisopropyl azodicarboxylate (0.39 ml) was added dropwise via syringe and the reaction was stirred at −78° C. for 45 mins. The reaction mixture was removed from the cold bath and allowed to warm to RT and stirred under N2 atmosphere overnight. Reaction mixture concentrated in vacuo. The residue was taken up in DCM (20 ml) and washed with water (20 mL). The 2 phases were separated, the organic extract was dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (496 mg). LC/MS MH+ 519, Rt 3.53 min (5 minute run)

Provenance & Evidence