m-Chloroperbenzoic acid → HCID 86746563, compound

HRID 2082323Notes

Reaction equation

ClC1C=C(C=CC=1)C(OO)=[O:6].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@H:14]([N:20]1[CH:33]=[CH:32][C:23]3[N:24]([CH3:31])[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[C:22]=3[C:21]1=[O:34])[CH2:13]2>ClCCl>[N:12]12[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]1)[CH:14]([N@@+:20]1([O-:6])[CH:33]=[CH:32][C:23]3[N:24]([CH3:31])[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=4[C:22]=3[C:21]1=[O:34])[CH2:13]2

Participants

Conditions

Temperature: 0 °C

Procedure

m-Chloroperoxybenzoic acid (1.2 g, 7.0 mmol) was added in small portions at 0° C. to a solution of (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)1,2-dihydro-5-methyl-1-oxopyrido[4,3-b]indole (1.8 g, 5.8 mmol), from Example 3, in dichloromethane (50 mL). The reaction mixture was stirred for additional 0.5 hour at 0° C. The solvent was removed under reduced pressure and the residue was purified by column chromatography (10% methanol in dichloromethane and 1% ammonium hydroxide) to afford 0.75 g (62% yield) of (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2-dihydro-5-methyl-1-oxopyrido[4,3-b]indole N-oxide, as an amorphous solid, m.p 98°-102° C.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (10% methanol in dichloromethane and 1% ammonium hydroxide)

Sources & evidence

ORD record: ord-6c5bbc480a7b45729eafb24025483c32
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189041

Reaction notes

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