erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline

Base Information

• Chemical Name: erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline
• CAS No.: 81531-49-9
• Molecular Formula: C₁₉H₂₀BrNO₄
• Molecular Weight: 406.276
• Mol file: 81531-49-9.mol

Synonyms:

Chemical Property of erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline

There total 6 articles about erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline 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: 90.0%

1-(2'-Bromo-5'-methoxybenzoyl)-2-methyl-3,4-dihydro-6,7-methylenedioxyisoquinolium iodide (81531-48-8) → erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline (81531-49-9,81531-50-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 4h;

Reference yield:

m-methoxyphenylacetic acid (1798-09-0) → erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline (81531-49-9,81531-50-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / Br₂, NaOAc / acetic acid / 3 h / ice-bath

2: 87 percent / 3 h / 180 °C

3: 73 percent / POCl₃ / toluene

4: 58 percent / active MnO₂ / CHCl₃ / 10 h

5: 95 percent / 6 h / Heating

6: 90 percent / NaBH₄ / ethanol / 4 h

With manganese(IV) oxide; sodium tetrahydroborate; bromine; sodium acetate; trichlorophosphate; In ethanol; chloroform; acetic acid; toluene;

Reference yield:

2-(2-bromo-5-methoxyphenyl)acetic acid (86826-93-9) → erythro/threo-1-(2'-Bromo-5'-methoxy-α-hydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-methylenedioxyisoquinoline (81531-49-9,81531-50-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / 3 h / 180 °C

2: 73 percent / POCl₃ / toluene

3: 58 percent / active MnO₂ / CHCl₃ / 10 h

4: 95 percent / 6 h / Heating

5: 90 percent / NaBH₄ / ethanol / 4 h

With manganese(IV) oxide; sodium tetrahydroborate; trichlorophosphate; In ethanol; chloroform; toluene;

upstream raw materials:

1-(2'-Bromo-5'-methoxybenzoyl)-2-methyl-3,4-dihydro-6,7-methylenedioxyisoquinolium iodide

m-methoxyphenylacetic acid

2-(2-bromo-5-methoxyphenyl)acetic acid

1-(2'-Bromo-5'-methoxybenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline

Downstream raw materials:

(+/-)-Oliveridine

(+/-)-Epioliveridine

Refernces

• 1、 Kessar, S. V.,Gupta, Y. P.,Mohammad, Taj. "Photocyclisation of 1-(2'-Halo-α-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolines; Synthesis of (+/-)-Oliveridine". . p. 984. Retrieved 2007/10/02.