(S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide

Base Information

• Chemical Name: (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide
• CAS No.: 1441209-67-1
• Molecular Formula: C₃₀H₃₆BrNO₄
• Molecular Weight: 554.524

Synonyms:(S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide

Chemical Property of (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide

Chemical Property:

Purity/Quality:

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Technology Process of (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide

There total 25 articles about (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide 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:

C23H33NO3 + 4-chlorobenzoyl chloride (586-75-4) → (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide (1441209-67-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.04.049

Reference yield:

4-isopropyl-2,3,5-trimethoxydihydrocinnamic acid (1217296-80-4) → (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide (1441209-67-1)

Guidance literature:

Multi-step reaction with 10 steps

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2.33 h / 0 °C / Inert atmosphere

2: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

3: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 - 70 °C / Inert atmosphere

4: potassium carbonate / acetone / 48 h / 20 - 65 °C / Inert atmosphere; Schlenk technique

5: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 65 °C / Inert atmosphere

6: sodium tetrahydroborate / ethanol / 3 h / 20 °C / Inert atmosphere

7: potassium hydrogensulfate / toluene / 4 h / 120 °C / Inert atmosphere

8: gallium(III) trichloride / toluene / 48 h / 100 °C / Inert atmosphere; Schlenk technique; Molecular sieve

9: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 65 °C / Inert atmosphere; Schlenk technique

10: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With gallium(III) trichloride; aluminum (III) chloride; sodium tetrahydroborate; potassium hydrogensulfate; lithium aluminium tetrahydride; oxalyl dichloride; lithium hydroxide monohydrate; potassium tert-butylate; potassium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2: |Friedel-Crafts Acylation / 3: |Claisen Condensation;

DOI:10.1016/j.tet.2013.04.049

Reference yield:

C15H21ClO4 → (S)-N-((8-isopropyl-6,7,9-trimethoxy-1-methyl-2,3,4,5-tetrahydro-1H-dibenzo[a,d][7]annulen-1-yl)methyl)-4-bromobenzamide (1441209-67-1)

Guidance literature:

Multi-step reaction with 9 steps

1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 1.5 h / 20 - 70 °C / Inert atmosphere

3: potassium carbonate / acetone / 48 h / 20 - 65 °C / Inert atmosphere; Schlenk technique

4: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 65 °C / Inert atmosphere

5: sodium tetrahydroborate / ethanol / 3 h / 20 °C / Inert atmosphere

6: potassium hydrogensulfate / toluene / 4 h / 120 °C / Inert atmosphere

7: gallium(III) trichloride / toluene / 48 h / 100 °C / Inert atmosphere; Schlenk technique; Molecular sieve

8: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 65 °C / Inert atmosphere; Schlenk technique

9: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With gallium(III) trichloride; aluminum (III) chloride; sodium tetrahydroborate; potassium hydrogensulfate; lithium aluminium tetrahydride; lithium hydroxide monohydrate; potassium tert-butylate; potassium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; 1: |Friedel-Crafts Acylation / 2: |Claisen Condensation;

DOI:10.1016/j.tet.2013.04.049

upstream raw materials:

(R)-tert-butyl 2-cyano-2-methyl-5-(triisopropylsilyloxy)pentanoate

4-chlorobenzoyl chloride

ethyl (4-isopropyl-2,3,5-trimethoxy)dihydrocinnamate

4-isopropyl-2,3,5-trimethoxydihydrocinnamic acid

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