11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene

Base Information

• Chemical Name: 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene
• CAS No.: 248276-31-5
• Molecular Formula: C₂₆H₂₄F₃N
• Molecular Weight: 407.478

Synonyms:11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene

Chemical Property of 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene

Chemical Property:

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Technology Process of 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene

There total 22 articles about 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.0^2,7]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: 23.0%

Trifluoro-methanesulfonic acid 11-benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-yl ester (248276-30-4) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-31-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In ethanol; at 90 ℃; for 18h;

DOI:10.1016/j.bmcl.2005.04.036

Reference yield:

cyclopent-3-enyl-(5-hydroxy-2-methoxy-phenyl)-methanone (861220-61-3) → 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-31-5)

Guidance literature:

Multi-step reaction with 9 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

8: 94 percent / pyridine / CH₂Cl₂

9: 23 percent / aq. Pd(PPh₃)4; KOAc / ethanol / 18 h / 90 °C

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (CH₂)5NCH₃O; Ph₃P(CH₂)3PPh₃; potassium acetate; boron trichloride; sodium tris(acetoxy)borohydride; ethylene glycol; triethylamine; hydrazine; palladium diacetate; In ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 3: Heck reaction / 4: Wolff-Kishner reduction / 9: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.04.036

Reference yield:

cyclopent-3-enyl-(2,5-dihydroxy-phenyl)-methanone → 11-benzyl-5-(4-trifluoromethyl-phenyl)-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene (248276-31-5)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂

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

3: 93 percent / N₂H₄; KOH; ethanediol / Heating

4: aq. OsO₄; (CH₂)5NCH₃O / acetone

5: aq. NaIO₄ / 1,2-dichloro-ethane

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

7: 94 percent / pyridine / CH₂Cl₂

8: 23 percent / aq. Pd(PPh₃)4; KOAc / ethanol / 18 h / 90 °C

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; (CH₂)5NCH₃O; Ph₃P(CH₂)3PPh₃; potassium acetate; sodium tris(acetoxy)borohydride; ethylene glycol; triethylamine; hydrazine; palladium diacetate; In ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 2: Heck reaction / 3: Wolff-Kishner reduction / 8: Suzuki coupling;

DOI:10.1016/j.bmcl.2005.04.036

upstream raw materials:

Trifluoro-methanesulfonic acid 11-benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2⁽⁷⁾,3,5-trien-5-yl ester

4-trifluoromethylphenylboronic acid

benzylamine

cyclopent-3-enyl-(5-hydroxy-2-methoxy-phenyl)-methanone

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