8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine

Base Information

• Chemical Name: 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine
• CAS No.: 125771-65-5
• Molecular Formula: C₂₆H₂₇NO₄
• Molecular Weight: 417.505
• Mol file: 125771-65-5.mol

Synonyms:

Chemical Property of 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine

There total 11 articles about 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine 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:

2-amino-1-(3-benzyloxy-4-methoxyphenyl)-ethanol (67387-79-5) → 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine (125771-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 54.1 percent / K₂CO₃, mol. sieves 3A / ethanol / 3 h / Heating

2: 79.5 percent / I₂, CF₃COOAg / CHCl₃ / 1 h

3: 72.5 percent / HCl / methanol / 7.5 h / Ambient temperature

4: 1) NaHCO₃, 2) NaBH₄ / 1) EtOH, 2 h, reflux, 2) EtOH, 2 h, reflux

5: 1) H₃BO₃, NaBH₄, 2) pyridine / 1) MeOH, 1 h, 2) RT, 18 h

6: 1) Ph₃P, (Ph₃P)2NiCl₂, Zn powder, KI / 1) DMF, 55 deg C, 30 min, 2) DMF, 55 deg C, 10 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; bis(triphenylphosphine)nickel(II) chloride; 3 A molecular sieve; iodine; boric acid; silver trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; potassium iodide; zinc; In methanol; ethanol; chloroform;

DOI:10.1248/cpb.37.1744

Reference yield:

(3-Benzyloxy-4-methoxy-phenyl)-hydroxy-acetonitrile (67387-77-3) → 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine (125771-65-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 29.5 percent / LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

2: 54.1 percent / K₂CO₃, mol. sieves 3A / ethanol / 3 h / Heating

3: 79.5 percent / I₂, CF₃COOAg / CHCl₃ / 1 h

4: 72.5 percent / HCl / methanol / 7.5 h / Ambient temperature

5: 1) NaHCO₃, 2) NaBH₄ / 1) EtOH, 2 h, reflux, 2) EtOH, 2 h, reflux

6: 1) H₃BO₃, NaBH₄, 2) pyridine / 1) MeOH, 1 h, 2) RT, 18 h

7: 1) Ph₃P, (Ph₃P)2NiCl₂, Zn powder, KI / 1) DMF, 55 deg C, 30 min, 2) DMF, 55 deg C, 10 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; bis(triphenylphosphine)nickel(II) chloride; lithium aluminium tetrahydride; 3 A molecular sieve; iodine; boric acid; silver trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; potassium iodide; zinc; In tetrahydrofuran; methanol; ethanol; chloroform;

DOI:10.1248/cpb.37.1744

Reference yield:

N-<2-Hydroxy-2-(3-benzyloxy-4-methoxyphenyl)ethyl>formamide (78004-26-9) → 8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine (125771-65-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 79.5 percent / I₂, CF₃COOAg / CHCl₃ / 1 h

2: 72.5 percent / HCl / methanol / 7.5 h / Ambient temperature

3: 1) NaHCO₃, 2) NaBH₄ / 1) EtOH, 2 h, reflux, 2) EtOH, 2 h, reflux

4: 1) H₃BO₃, NaBH₄, 2) pyridine / 1) MeOH, 1 h, 2) RT, 18 h

5: 1) Ph₃P, (Ph₃P)2NiCl₂, Zn powder, KI / 1) DMF, 55 deg C, 30 min, 2) DMF, 55 deg C, 10 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; bis(triphenylphosphine)nickel(II) chloride; iodine; boric acid; silver trifluoroacetate; sodium hydrogencarbonate; triphenylphosphine; potassium iodide; zinc; In methanol; chloroform;

DOI:10.1248/cpb.37.1744

upstream raw materials:

O-acetyl-β-(4-benzyloxy-2-bromo-5-methoxyphenyl)-N-(2-bromobenzyl)-N-methylethanolamine

O-acetyl-β-(5-benzyloxy-2-iodo-4-methoxyphenyl)-N-(2-iodobenzyl)-N-methylethanolamine

2-iodobenzaldehyde

2-amino-1-(3-benzyloxy-4-methoxyphenyl)-ethanol

Downstream raw materials:

10-benzyloxy-8-hydroxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine