Cyclohexanol → HCID 53949242、化合物

反応式

[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]=1

参加物

反応物 3

HCID 7966Cyclohexanol

HCID 9032Potassium Cyanide

HCID 54197869HCID 54197869、化合物

生成物 1

HCID 53949242HCID 53949242、化合物

実験手順

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°.