(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → HCID 86622337, compound

Participants

Reaction Conditions

Reaction Steps

Step AE (4): A solution of tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (298 mg) and LiClO4 (mg) in acetonitrile (3.0 mL) was stirred at rt for 10 min. To the above solution was added 1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine from Step AE (3) (137 mg) in acetonitrile (0.50 mL), and the reaction mixture was heated at 45° C. for 36 h. Solvents were removed in vacuo, and the residue was purified by HPLC to give tert-butyl (2S,3R)-4-((1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate as an oil (77 mg). retention time: 1.85 min (method B). MS (ESI) (M+H)+ 483.30.

Provenance & Evidence