Cyclohexanol → HCID 53949242, compound
Reaction equation
[Br: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.[CH:25]1(O)[CH2:30]CC[CH2:27][CH2:26]1.[C-]#N.[K+]>>[Br: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][CH:19]3[CH2:27][CH2:26][CH2:25][CH2:30][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Procedure
A mixture of 9.50 g (24.3 mmol) of ethyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate, 60 ml (560 mmol) of cyclohexanol and 300 mg of powdered potassium cyanide is stirred at 130° for 24 hours, a small amount of cyclohexanol being distilled off from time to time. The solution obtained is subsequently evaporated to dryness, the residue is taken up in chloroform, washed with water and dried over magnesium sulphate. After removal of the solvent, the residue is chromatographed on a silica gel column while eluting with ethyl acetate and subsequently recrystallized from ethyl acetate. There is obtained cyclohexyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 167°-168°.
Workup
- distillationa small amount of cyclohexanol being distilled off from time to time
- customThe solution obtained
- customis subsequently evaporated to dryness
- washwashed with water
- dry with materialdried over magnesium sulphate
- customAfter removal of the solvent
- customthe residue is chromatographed on a silica gel column
- washwhile eluting with ethyl acetate
- customsubsequently recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-df5bc6f6430b4e0f833ea224270078a3
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04489003
Reaction notes
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