Acetone → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2,3-dihydroxy-propyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Participants

Reaction Steps

To a mixture of racemic (2′R,3R,4′S)-1′-allyl-6-bromo-4′-(3-chlorophenyl)-2′-(1-methyl cyclopropyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (100 mg, 0.16 mmol), N-methylmorpholine N-oxide (30 mg, 0.22 mmol) and 3 drops of water in acetone (3 mL) was added OsO4 (10 mg, 0.04 mmol). The mixture was stirred at room temperature for 1 h, then purified by Prep-HPLC to give the title compound as a white solid (40 mg, 37%).

Provenance & Evidence