4-Methoxybenzyl alcohol → HCID 53977518, compound
Reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].[CH3:28][O:29][C:30]1[CH:37]=[CH:36]C(CO)=[CH:32][CH:31]=1>>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][C:20]3[CH:36]=[CH:37][C:30]([O:29][CH3:28])=[CH:31][CH:32]=3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Procedure
A mixture of 3.45 g (10 mmol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 100 mg (1.5 mmol) of potassium cyanide and 20 ml of 4-methoxybenzyl alcohol is stirred at 110° for 3.5 days, the resulting ethanol being removed in vacuo from time to time. The solvent is subsequently removed by distillation in a high vacuum, the residue is taken up in methylene chloride, the methylene chloride solution is washed three times with water, dried over magnesium sulphate and evaporated. The crude product is chromatographed on silica gel while eluting with ethyl acetate. By recrystallization from ethyl acetate there is obtained p-methoxybenzyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 185°-186°.
Workup
- customthe resulting ethanol being removed in vacuo from time to time
- customThe solvent is subsequently removed by distillation in a high vacuum
- washthe methylene chloride solution is washed three times with water
- dry with materialdried over magnesium sulphate
- customevaporated
- customThe crude product is chromatographed on silica gel
- washwhile eluting with ethyl acetate
- customBy recrystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-fd4e105bf82948759e92bb7a82adb273
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04489003
Reaction notes
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