11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester

Base Information

• Chemical Name: 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester
• CAS No.: 248276-34-8
• Molecular Formula: C₂₁H₂₃NO₂
• Molecular Weight: 321.419

Synonyms:11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester

Chemical Property of 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester

There total 16 articles about 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2⁽⁷⁾,3,5-triene-5-carboxylic acid methyl ester 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: 38.0%

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) + potassium acetate (127-08-2) → 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2(7),3,5-triene-5-carboxylic acid methyl ester (248276-34-8)

Guidance literature:

With carbon monoxide; Ph₃P(CH₂)3PPh₃; TEA; palladium diacetate; In methanol; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2005.04.036

Reference yield:

cyclopent-3-enyl-(5-hydroxy-2-methoxy-phenyl)-methanone (861220-61-3) → 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2(7),3,5-triene-5-carboxylic acid methyl ester (248276-34-8)

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: 38 percent / TEA; Ph₃P(CH₂)3PPh₃; CO / Pd(OAc)2 / dimethylsulfoxide; methanol

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

DOI:10.1016/j.bmcl.2005.04.036

Reference yield:

cyclopent-3-enyl-(2,5-dihydroxy-phenyl)-methanone → 11-benzyl-11-aza-tricyclo[7.3.1.02.7]trideca-2(7),3,5-triene-5-carboxylic acid methyl ester (248276-34-8)

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: 38 percent / TEA; Ph₃P(CH₂)3PPh₃; CO / Pd(OAc)2 / dimethylsulfoxide; methanol

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

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

potassium acetate

benzylamine

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

Downstream raw materials:

2-(11-benzyl-11-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-5-yl)-propan-2-ol

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