O-Methylarmepavine, (R)-

Base Information

• Chemical Name: O-Methylarmepavine, (R)-
• CAS No.: 5701-00-8
• Molecular Formula: C₂₀H₂₅NO₃
• Molecular Weight: 327.423
• UNII: V8Z37NT8TT
• DSSTox Substance ID: DTXSID00205619
• Nikkaji Number: J1.488.060G
• Wikidata: Q83079230
• Mol file: 5701-00-8.mol

Synonyms:O-methylarmepavine

Chemical Property of O-Methylarmepavine, (R)-

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 327.18344366
• Heavy Atom Count: 24
• Complexity: 383

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)OC)OC)OC

Technology Process of O-Methylarmepavine, (R)-

There total 30 articles about O-Methylarmepavine, (R)- 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: 78.0%

(R)-1-(4'-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (60383-76-8) + dimethyl dicarbonate (4525-33-1) → (R)-O-methylarmepavine (5701-00-8,13425-06-4)

Guidance literature:

(R)-1-(4'-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; dimethyl dicarbonate; In dichloromethane; at 20 ℃; for 0.333333h;

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.333333h; Further stages.;

DOI:10.1021/jo001397s

Reference yield:

4-Methoxyphenylacetaldehyde (5703-26-4) → (R)-O-methylarmepavine (5701-00-8,13425-06-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 83 percent / 120 °C

2.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C

2.2: 81 percent / Et₂AlCl / hexane / -90 - 20 °C

3.1: PCC; NaOAc; 3A molecular sieves / CH₂Cl₂ / 48 h / 20 °C

3.2: 55 percent / KOH / tetrahydrofuran

4.1: CH₂Cl₂ / 0.33 h / 20 °C

4.2: 78 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

With 3 A molecular sieve; tert.-butyl lithium; sodium acetate; pyridinium chlorochromate; In diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo001397s

Reference yield:

2-bromo-3,4-dimethoxybenzylaldehyde (55171-60-3) → (R)-O-methylarmepavine (5701-00-8,13425-06-4)

Guidance literature:

Multi-step reaction with 7 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

5.1: t-BuLi / diethyl ether; pentane / 0.17 h / -90 °C

5.2: 81 percent / Et₂AlCl / hexane / -90 - 20 °C

6.1: PCC; NaOAc; 3A molecular sieves / CH₂Cl₂ / 48 h / 20 °C

6.2: 55 percent / KOH / tetrahydrofuran

7.1: CH₂Cl₂ / 0.33 h / 20 °C

7.2: 78 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

With sodium tetrahydroborate; 3 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tert.-butyl lithium; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/jo001397s

upstream raw materials:

(+)-isotetrandrine

diazomethane

pheanthine

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

Downstream raw materials:

N,O-dimethyl-N-norarmepavine methyliodide

Refernces

• 1、 Xie, Zhiyu,Liu, Lei,Chen, Wenfang,Zheng, Hongbo,Xu, Qingqing,Yuan, Huiqing,Lou, Hongxiang. "Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates". supporting information. p. 3904 - 3908. Retrieved 2014/05/06.
• 2、 Pedrosa,Andres,Iglesias. "A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids". . p. 243 - 250. Retrieved 2007/10/03.