Water → 6-chloro-4'-[5-chloro-2-(1-hydroxycarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Reaction Steps

A mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-2′-(5-chloro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (280 mg, 0.41 mmol), LiOH.H2O (1 g, 24.6 mmol), H2O (12 mL) and methanol (38 mL) was refluxed for 2 h. After cooled to room temperature, the solution was concentrated and then the mixture was acidified to “pH” 1-2 by addition of concentrated HCl solution and then extracted with EtOAc. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow solid (220 mg).

Provenance & Evidence