N-[1-((1R,2S)-2-Dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide → 7-((1R,2S)-2-dibenzylamino-1-hydroxy-3-phenylpropyl)-1,5,6,7-tetrahydroazepin-2-one

Participants

Reaction Steps

Dissolve N-[1-((1R,2S)-2-dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide (0.5 g, 1.06 mmol) in dichloromethane (50 mL) under nitrogen atmosphere and add Grubb's second generation catalyst (20% mol). Stir the reaction at 50° C. for one day. Concentrate under reduced pressure. Purify on silica gel with hexane/ethyl acetate mixtures to give a mixture of two products. (0, 210 g, 45%) that may be separated using HPLC-MS (19×300 mm, 7 μm, C-18 column; flow rate=20 mL/min; mobile phase gradient 5%-95% over 26 minutes; Solvent A: acetonitrile; Solvent B: 0.1% trifluoroacetic acid in water).

Provenance & Evidence