Borane → 3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
Reaction equation
B.[BH4-].[Na+].[Cl-].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]([CH:36]([CH3:38])[CH3:37])([C:34]#[N:35])[CH2:16][CH2:17][CH2:18][C:19]2[CH2:28][C:27]3[C:22](=[CH:23][C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[CH:26]=3)[CH2:21][N+:20]=2[CH3:33])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]>CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]([CH:36]([CH3:38])[CH3:37])([C:34]#[N:35])[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:28][C:27]3[C:22](=[CH:23][C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[CH:26]=3)[CH2:21][N:20]2[CH3:33])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The dihydroisoquinolinium salt of formula 34 is then hydrogenated to produce a compound of formula 1 (step 6). This reaction is performed using a suitable hydrogenating agent, preferably a boron hydride derivative, particularly NaBH4. The solvent used is preferably a lower alkanol, particularly MeOH. The reaction is carried out at a temperature of about -10° C. to about 50° C., preferably about 0° C., over about 10 minutes to about 3 hours, preferably 1 hour. For example, 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,4-dihydroisoquinolinium chloride (34) is suspended in MeOH at 0° C., then treated with NaBH4 for about 1 hour to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1).
Sources & evidence
- ORD record
- ord-76f0901702ae4023b43e084996bd467f
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04667038
Reaction notes
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