(1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene

Base Information

• Chemical Name: (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene
• CAS No.: 328242-17-7
• Molecular Formula: C₁₉H₂₁NO
• Molecular Weight: 279.382

Synonyms:(1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene

Chemical Property of (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene

Chemical Property:

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Technology Process of (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene

There total 4 articles about (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[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: 44.0%

(1S)-pinocarvone (19890-00-7) + 1-<2-(2-Methoxyphenyl)-2-oxyethyl>pyridinium iodide → (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2(7),3,5-triene (328242-17-7)

Guidance literature:

With ammonium acetate; In acetic acid; at 120 ℃; for 4h;

DOI:10.1016/S0040-4020(01)01002-X

Reference yield:

2-Methoxyacetophenone (579-74-8) → (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2(7),3,5-triene (328242-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine / 3 h / 100 - 110 °C

2: ammonium acetate; acetic acid / 20 h / 100 - 110 °C / Inert atmosphere

With ammonium acetate; iodine; acetic acid;

DOI:10.1002/jccs.201100474

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → (1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2(7),3,5-triene (328242-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C

1.2: 60 h

2.1: iodine / 3 h / 100 - 110 °C

3.1: ammonium acetate; acetic acid / 20 h / 100 - 110 °C / Inert atmosphere

With lithium hydroxide monohydrate; ammonium acetate; iodine; acetic acid; In tetrahydrofuran;

DOI:10.1002/jccs.201100474

upstream raw materials:

(1S)-pinocarvone

2-Methoxyacetophenone

o-hydroxyacetophenone

(-)-α-pinene

Downstream raw materials:

(1S,8R,9S)-8-isopropyl-5-(2-methoxy-phenyl)-10,10-dimethyl-6-aza-tricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene

2-((1S,8R,9S)-8-isopropyl-10,10-dimethyl-6-aza-tricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-trien-5-yl)-phenol

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

C₂₀H₂₁NO₃

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