[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:21])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[C:19]#N)[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:28](OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:21])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH2:19][CH3:28])[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1
10-Chloro-3-cyano-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine (6.41 g) was dissolved in 300 ml of tetrahydrofuran, and with stirring, 4.06 g of lithium aluminum hydride was added, under nitrogen. The suspension was heated at reflux for 2 hr and ethyl acetate was added dropwise. To the mixture was added water, 15% aqueous sodium hydroxide solution, and water. The suspension was filtered, and the filtrate was concentrated. The residue was triturated with ether. The mother liquor was concentrated and 2-g portions of the residue were alkylated with phenethyl bromide and 4-bromo-2-methylbut-2-ene according to the procedures described in Examples 23 and 26 to give 0.35 g (20%) and 0.41 g (24%), respectively, of product. Column chromatography (alumina, ether) followed by recrystallization from dichloromethane-ether-pentane afforded the analytical sample, mp 208°-210° C. (dec.).
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