Sodium borohydride → 3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

HRID 979375Notes

Reaction equation

HRID 979375 reaction equation
[BH4-].[Na+].[I-].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]([CH:35]([CH3:37])[CH3:36])([C:33]#[N:34])[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[CH:25]=3)[CH:20]=[N+:19]2[CH3:32])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]([CH:35]([CH3:37])[CH3:36])([C:33]#[N:34])[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:30][CH3:31])=[C:24]([O:28][CH3:29])[CH:25]=3)[CH2:20][N:19]2[CH3:32])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 202022113-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodide

Product 1

HCID 1291023-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The resulting compound of formula 41 is then hydrogenated to produce a compound of formula 1. This hydrogenation is preferably performed using 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-3,4-dihydroisoquinolinium iodide (41) 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-3e0d27dc110e4f999382de9521095820
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

Loading…