HCID 15518231, compound → HCID 11721210, compound

HRID 635523Notes

Reaction equation

[CH2:1]1[O:43][C:4]2=[CH:5][C:6]3[C:19]4[N:18](C)[CH:17]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C:16]5[C:11](=[CH:12][CH:13]=[C:14]([O:40][CH3:41])[C:15]=5[O:32][CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:10]=4[CH:9]=[CH:8][C:7]=3[CH:42]=[C:3]2[O:2]1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]1[O:43][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:21][CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[N:18]=4)[C:15]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([O:40][CH3:41])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:42]=[C:3]2[O:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

After 2,3-(methylenedioxy)-5-methyl-6-[3-(t-butyldimethylsiloxy)propyl]-7-benzyloxy-8-methoxy-5, 6-dihydrobenzo[c]phenanthridine (871 mg, 1.46 mmol) was dissolved in toluene (30 mL), activated manganese dioxide (4.36 g) was added to the solution. The mixture was stirred at 100° C. for 2 hours. Manganese dioxide was removed by filtration. Thereafter, the filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluted with 33-66% methylene chloride-hexane) to provide 2,3-(methylenedioxy)-6-[3-(t-butyldimethylsiloxy)propyl]-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (457 mg, yield 54%) as colorless powders.

Workup

customManganese dioxide was removed by filtration
concentrationThereafter, the filtrate was concentrated in vacuo
customThe resulting residue was purified by silica gel column chromatography (eluted with 33-66% methylene chloride-hexane)

Sources & evidence

ORD record: ord-5cfa8f4cf1e34a6d9d5ee68b0c4ca458
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06187783B1

Reaction notes

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