3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

Base Information

• Chemical Name: 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
• CAS No.: 321669-88-9
• Molecular Formula: C₂₉H₄₀BrNO₄
• Molecular Weight: 546.545
• Mol file: 321669-88-9.mol

Synonyms:3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

Chemical Property of 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine

There total 5 articles about 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 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: 83.0%

4-Methoxyphenylacetaldehyde (5703-26-4) + N-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-8-aminomenthol (321669-67-4) → 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (321669-88-9)

Guidance literature:

at 120 ℃;

DOI:10.1021/jo001397s

Reference yield:

2-bromo-3,4-dimethoxybenzylaldehyde (55171-60-3) → 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (321669-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 12 h / 20 °C

1.3: 90 percent / formic acid / CH₂Cl₂ / 72 h / 20 °C

2.1: 95 percent / CH₂Cl₂ / 20 °C

3.1: NaBH₄; BF₃*OEt₂ / tetrahydrofuran / 2 h / 20 °C

3.2: 90 percent / NaOH / H₂O / 1 h / Heating

4.1: 83 percent / 120 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; potassium tert-butylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo001397s

Reference yield:

2-(4-Methoxyphenyl)ethanol (702-23-8) → 3-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-2α-(p-methoxybenzyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine (321669-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: PCC / CH₂Cl₂ / 3 h / cooling

2: 83 percent / 120 °C

With pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jo001397s

upstream raw materials:

4-Methoxyphenylacetaldehyde

N-[(2'-bromo-4',5'-dimethoxyphenyl)ethyl]-8-aminomenthol

2-bromo-3,4-dimethoxybenzylaldehyde

2-(4-Methoxyphenyl)ethanol

Downstream raw materials:

(R)-O-methylarmepavine

(R)-1-(4'-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

(1R)-N-(8-menthyl)-1-(p-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline