11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene

Base Information

• Chemical Name: 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene
• CAS No.: 248276-28-0
• Molecular Formula: C₂₀H₂₃NO₂
• Molecular Weight: 309.408

Synonyms:11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene

Chemical Property of 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene

Chemical Property:

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Technology Process of 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene

There total 18 articles about 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-triene 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: 64.0%

C26H36BNO3 → 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-28-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.04.036

Reference yield:

11-benzyl-6-bromo-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-26-8) + aq. hydrogen peroxide + aq. NaHSO3 + Triisopropyl borate (5419-55-6) → 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-28-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

Reference yield:

cyclopent-3-enyl-(2-hydroxy-6-methoxy-phenyl)-methanone (248275-72-1) → 11-benzyl-6-hydroxy-5-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-28-0)

Guidance literature:

Multi-step reaction with 7 steps

1: BCl₃ / CH₂Cl₂

2: pyridine / CH₂Cl₂

3: Ph₃P(CH₂)3PPh₃; KOAc; Et₃N / Pd(OAc)2 / dimethylformamide / 110 °C

4: 93 percent / N₂H₄; KOH; ethanediol / Heating

5: aq. OsO₄; (CH₂)5NCH₃O / acetone

6: aq. NaIO₄ / 1,2-dichloro-ethane

7: NaBH(OAc)3 / 1,2-dichloro-ethane

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; (CH₂)5NCH₃O; Ph₃P(CH₂)3PPh₃; potassium acetate; boron trichloride; sodium tris(acetoxy)borohydride; ethylene glycol; triethylamine; hydrazine; palladium diacetate; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 3: Heck reaction / 4: Wolff-Kishner reduction;

DOI:10.1016/j.bmcl.2005.04.036

upstream raw materials:

benzylamine

cyclopent-3-enyl-(2-hydroxy-6-methoxy-phenyl)-methanone

cyclopent-3-enyl-(2,6-dimethoxy-phenyl)-methanone

1-hydroxy-2-methoxy-5,8-dihydro-5,8-methano-benzocyclohepten-9-one

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