[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]2)[CH:7]=1.[ClH:25]>C(O)C>[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:8]2[CH2:17][C:16]3[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=3[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]2)[CH:7]=1A solution of (−)-7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (1.5 g) in ethanol (20 ml) was combined with concentrated hydrochloric acid (1.2 ml) and concentrated. The resultant crystal was recrystallized from a solvent mixture of ethanol and water to obtain (−)-7-(5-fluoro-2-methylphenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound E) (0.96 g, 99.3% ee). (This compound was proven to have an absolute configuration of an S form based in an X-ray crystal structure analysis.)
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