1-Acetoxy-2-bromoethane → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2-hydroxyethyl)-2'-isopropenyl-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)-6-bromo-4′-(3-chlorophenyl)-2′-isopropenyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (150 mg, 0.26 mmol) and acetic acid 2-bromo-ethyl ester (867 mg, 5.22 mmol) was added LiH (63 mg, 7.9 mmol). The mixture was stirred at room temperature for 20 h, then diluted with ethyl acetate (10 mL), quenched with water (10 mL). The organic layer was separated, washed with water for 5 times, dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give product (57 mg).

Provenance & Evidence