Potassium Cyanide → trans-2-methylcyclohexyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 1154460Notes

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](OCC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]1[OH:32].[C-]#N.[K+]>>[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:32][C@@H:27]3[CH2:28][CH2:29][CH2:30][CH2:31][C@H:26]3[CH3:25])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 9032Potassium Cyanide

HCID 24004trans-2-Methylcyclohexanol

HCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

Product 1

HCID 86739835trans-2-methylcyclohexyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Procedure

A mixture of 3.45 (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, 11.4 g (100 mmol) of trans-2-methylcyclohexanol and 100 mg of powdered potassium cyanide is stirred at 130° for 6 hours, the solution obtained is evaporated to dryness and the residue is chromatographed on a silica gel column. By recrystallization from ethyl acetate there is obtained trans-2-methylcyclohexyl (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 213°-215° (1:1 mixture of the two diastereoisomers).

Workup

customthe solution obtained
customis evaporated to dryness
customthe residue is chromatographed on a silica gel column
customBy recrystallization from ethyl acetate

Sources & evidence

ORD record: ord-f3c02cd747eb4cf8a5ca456175487bef
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04489003

Reaction notes

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