(+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 204395-64-2
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37
• Mol file: 204395-64-2.mol

Synonyms:(+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline

There total 5 articles about (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(S)-2-[N-(3,4-dimethoxybenzyl)-N-methyl]amino-2-phenylacetaldehyde (204395-63-1) → (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline (204395-64-2)

Guidance literature:

With hydrogenchloride; In acetone; for 0.25h; Yield given; Ambient temperature;

DOI:10.1016/S0957-4166(97)00607-1

Reference yield:

(-)-(1'S)-(E)-N-(2-hydroxy-1-phenylethyl)-3,4-dimethoxybenzylideneamine (195311-96-7) → (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline (204395-64-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / NaBH₄ / methanol / 3 h / Ambient temperature

2: 100 percent / molecular sieves 4 Angstroem / CH₂Cl₂; H₂O / 0.25 h / Ambient temperature

3: 80 percent / NaBH₃CN / acetonitrile / 28 h / Ambient temperature

4: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -60 deg C, 15 min

5: conc. aq. HCl / acetone / 0.25 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; sodium cyanoborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0957-4166(97)00607-1

Reference yield:

(+)-(4S)-N-(3,4-dimethoxybenzyl)-4-phenyloxazolidine (204395-61-9) → (+)-(3S,4S)-6,7-dimethoxy-4-hydroxy-2-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline (204395-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaBH₃CN / acetonitrile / 28 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -60 deg C, 15 min

3: conc. aq. HCl / acetone / 0.25 h / Ambient temperature

With hydrogenchloride; oxalyl dichloride; sodium cyanoborohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In acetone; acetonitrile;

DOI:10.1016/S0957-4166(97)00607-1

upstream raw materials:

(S)-2-[N-(3,4-dimethoxybenzyl)-N-methyl]amino-2-phenylacetaldehyde

(-)-(1'S)-(E)-N-(2-hydroxy-1-phenylethyl)-3,4-dimethoxybenzylideneamine

(+)-(2S)-2-[N-(3,4-dimethoxybenzyl)-N-methyl]amino-2-phenylethanol

(+)-(4S)-N-(3,4-dimethoxybenzyl)-4-phenyloxazolidine