(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

Base Information

• Chemical Name: (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
• CAS No.: 328242-18-8
• Molecular Formula: C₂₂H₂₇NO
• Molecular Weight: 321.462

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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: 56.0%

isopropyl bromide (75-26-3) + (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) → (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 (328242-18-8)

Guidance literature:

(1S,9S)-5-(2-methoxyphenyl)-10,10-dimethyl-6-azatricyclo[7.1.1.0(2,7)]undeca-2⁽⁷⁾,3,5-triene; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

isopropyl bromide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1002/jccs.201100474

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → (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 (328242-18-8)

Guidance literature:

Multi-step reaction with 4 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

4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C

4.2: -78 - 20 °C

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

DOI:10.1002/jccs.201100474

Reference yield:

2-Methoxyacetophenone (579-74-8) → (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 (328242-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iodine / 3 h / 100 - 110 °C

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

3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C

3.2: -78 - 20 °C

With ammonium acetate; iodine; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1002/jccs.201100474

upstream raw materials:

2-Methoxyacetophenone

o-hydroxyacetophenone

isopropyl bromide

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

Downstream raw materials:

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

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