(+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Base Information

• Chemical Name: (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• CAS No.: 80601-70-3
• Molecular Formula: C₂₇H₂₉NO₇
• Molecular Weight: 479.53
• Mol file: 80601-70-3.mol

Synonyms:(+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property of (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

There total 1 articles about (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-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: 85.0%

trimetoquinol (21650-42-0) + benzyl chloroformate (501-53-1,94274-21-2) → (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (80601-70-3)

Guidance literature:

With sodium hydrogencarbonate; In chloroform; water; at 5 ℃; for 1h; then 2 h room temperature;

DOI:10.1248/cpb.29.2816

Reference yield: 87.0%

N,N-dimethyl(methylene)ammonium chloride (30354-18-8) + (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (80601-70-3) → (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-5-dimethylaminomethyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (344746-45-8)

Guidance literature:

With triethylamine; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1248/cpb.29.2816

Reference yield:

(+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (80601-70-3) → (+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-5-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (80601-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N / acetonitrile / 1 h / 0 °C

2: 1.) Me₂SO₄, 2.) NaBH₃CN / 1.) HMPA, 50 deg C, 1.5 h, 2.) HMPA, 70 deg C, 2 h

With sodium cyanoborohydride; triethylamine; dimethyl sulfate; In acetonitrile;

DOI:10.1248/cpb.29.2816

upstream raw materials:

trimetoquinol

benzyl chloroformate

Downstream raw materials:

(+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-5-dimethylaminomethyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline

(+/-)-N-benzyloxycarbonyl-6,7-dihydroxy-5-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline