(1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

Base Information

• Chemical Name: (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene
• CAS No.: 349472-96-4
• Molecular Formula: C₁₉H₂₀FN
• Molecular Weight: 281.373

Synonyms:(1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

Chemical Property of (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

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Technology Process of (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

There total 3 articles about (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-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: 63.0%

(1R,9R)-5-(2-Fluoro-phenyl)-10,10-dimethyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (349472-95-3) + methyl iodide (74-88-4) → (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (349472-96-4)

Guidance literature:

(1R,9R)-5-(2-Fluoro-phenyl)-10,10-dimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene; With n-butyllithium; In tetrahydrofuran; at -30 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -50 ℃; for 4h;

DOI:10.1016/S0040-4039(01)00369-0

Reference yield:

2'-Fluoroacetophenone (445-27-2) → (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (349472-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 47 percent / I₂ / 2 h / 100 °C

2.1: 73 percent / AcONH₄ / acetic acid / 5 h / 90 °C

3.1: n-BuLi / tetrahydrofuran / 1 h / -30 °C

3.2: 63 percent / tetrahydrofuran / 4 h / -50 °C

With n-butyllithium; ammonium acetate; iodine; In tetrahydrofuran; acetic acid; 2.1: Kroehnke annulation;

DOI:10.1016/S0040-4039(01)00369-0

Reference yield:

1-[2-(2-fluorophenyl)-2-oxoethyl]pyridinium iodide → (1R,8S,9R)-5-(2-Fluoro-phenyl)-8,10,10-trimethyl-6-aza-tricyclo[7.1.1.02,7]undeca-2(7),3,5-triene (349472-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 73 percent / AcONH₄ / acetic acid / 5 h / 90 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -30 °C

2.2: 63 percent / tetrahydrofuran / 4 h / -50 °C

With n-butyllithium; ammonium acetate; In tetrahydrofuran; acetic acid; 1.1: Kroehnke annulation;

DOI:10.1016/S0040-4039(01)00369-0

upstream raw materials:

(1R,9R)-5-(2-Fluoro-phenyl)-10,10-dimethyl-6-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene

methyl iodide

2'-Fluoroacetophenone

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