Cyclopentanol → HCID 20434809, compound

HRID 1154457Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][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+].[CH:26]1(O)[CH2:30]CC[CH2:27]1>>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH:19]3[CH2:30][CH2:26][CH2:27][CH2:20]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7298Cyclopentanol

HCID 9032Potassium Cyanide

HCID 71231Sarmazenil

Product 1

HCID 20434809HCID 20434809, compound

Procedure

3.19 g (10 mmol) of ethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 70 mg of powdered potassium cyanide and 10 ml of cyclopentanol are stirred at 120° overnight, subsequently evaporated and the residue is chromatographed on silica gel while eluting with ethyl acetate. By recrystallization from ethyl acetate there is obtained cyclopentyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 162°-163°.

Workup

customsubsequently evaporated
customthe residue is chromatographed on silica gel
washwhile eluting with ethyl acetate
customBy recrystallization from ethyl acetate

Sources & evidence

ORD record: ord-ad0fa2d2154a4f4fa3d460dddc75e098
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04489003

Reaction notes

Loading…