[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2([C:26]#N)[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13]1.Cl.C([O:32]C(C)C)(C)C>C1(C)C=CC=CC=1.CO>[CH3:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2([CH:26]=[O:32])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13]1The reaction is performed under a dry nitrogen atmosphere. 94.4 cm3 (0.0944 mol) of a 1N toluene solution of diisobutylaluminium hydride are added at -60° C. to a solution of 13.3 g (0.059 mol) of 1-(1-methyl-3-indolyl)-cyclopentanecarbonitrile in 230 cm3 of toluene. The temperature of the mixture is thereafter allowed to rise to room temperature, and the reaction is then stopped by adding 50 cm3 of methanol and then 230 cm3 of 3N hydrochloric acid to the reaction mixture. The mixture is extracted with dichloromethane, the organic extract is washed with water, dried over sodium sulphate and filtered and the filtrate is evaporated. In succession, the residue obtained is taken up with diisopropyl ether, some insoluble matter is removed by filtration, the solvent is evaporated and the residue is crystallised in hexane.
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