ClCC([C:5]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:14])[C:9]3[C:15](=[O:18])[CH2:16][CH2:17][C:8]=3[C:7]=2[CH:6]=1)=O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl:27][C:28]1C=CC=C(C(OO)=O)C=1.[C:38]([O-:41])(O)=[O:39].[Na+]>C(Cl)(Cl)Cl>[Cl:27][CH2:28][C:38]([O:41][C:5]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:14])[C:9]3[C:15](=[O:18])[CH2:16][CH2:17][C:8]=3[C:7]=2[CH:6]=1)=[O:39]To a stirred solution of 7-chloroacetyl-1,4-dihydro-4-methylcyclopent[b]indol-3(2H)-one (2.0 g) in chloroform (100 ml) was added sodium phosphate (1.02 g) followed by m-chloroperbenzoic acid (2.5 g, 50-60% purity). The mixture was stirred at room temperature under a nitrogen atmosphere for 14 hours. Saturated NaHCO3 aqueous solution (50 ml) was added, the layers separated and the organic layer washed with water (2×50 ml). The solution was dried (Na2SO4), filtered and concentrated to give a yellow oil which crystallized upon standing. Recrystallization from with EtOH provided 7-chloroacetyloxy-1,4-dihydro-4-methylcyclopent[b]indol-3(2H)-one (1.1 g).
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