Diiodomethane → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-2'-(1-ethyl-cyclopropyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

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Reaction Steps

CH2I2 (1.2 g, 4.6 mmol) was dissolved in dry toluene (5 mL) at 0° C. After stirred for 10 min under Argon, Et2Zn (1 M in THF, 3.3 mL, 3.67 mmol) was added. After stirred for 15 min, a solution of racemic (2′R,3R,4′S)-6-bromo-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (270 mg, 0.46 mmol) prepared in example 161b in dry toluene (10 mL) was added. After stirred at room temperature for 3 h, the reaction was quenched with saturated NH4Cl (20 mL). The aqueous layer was extracted with EtOAc. The combined organic layer was dried over Na2SO4, concentrated, the residue, was used for next step without further purification.

Provenance & Evidence