Acetic Anhydride → 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one
Reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][CH:9]([C:25]1[N:26]=[CH:27][N:28]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]=1[CH3:30])[CH:10]1[C:23](=[O:24])[N:14]2[C:15]3[C:20]([C:21]([CH3:22])=[C:13]2[CH2:12][CH2:11]1)=[CH:19][CH:18]=[CH:17][CH:16]=3>N1C=CC=CC=1>[C:1]([O:8][CH:9]([C:25]1[N:26]=[CH:27][N:28]([C:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:29]=1[CH3:30])[CH:10]1[C:23](=[O:24])[N:14]2[C:15]3[C:20]([C:21]([CH3:22])=[C:13]2[CH2:12][CH2:11]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Acetic anhydride (5 ml) was added to a solution of 8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (4 g, a mixture of the isomers A and B) in pyridine (50 ml). After being stirred at room temperature for 20 hours, the solution was evaporated in vacuo. Silica gel column chromatography (1% methanol-methylene chloride) of the oil obtained gave 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (4.30 g) as an amorphous powder.
Workup
- customthe solution was evaporated in vacuo
- customSilica gel column chromatography (1% methanol-methylene chloride) of the oil obtained
Sources & evidence
- ORD record
- ord-20152ff630b440d9ae5c2bc9a9ac50ba
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05290785
Reaction notes
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