4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester
• CAS No.: 557056-05-0
• Molecular Formula: C₃₅H₅₉N₃O₇
• Molecular Weight: 633.869

Synonyms:4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester

There total 7 articles about 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl 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:

6-bromo-1-hexanenitrile (6621-59-6) → 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester (557056-05-0)

Guidance literature:

Multi-step reaction with 6 steps

1: xylene / Heating

2: 62 percent / KN(TMS)2 / tetrahydrofuran; toluene / 4 h

3: 87 percent / H₂ / Pd/C / ethanol / 2 h / 760 Torr

4: 73 percent / sodium tert-butoxide; 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; tris(dibenzylideneacetone)dipalladium / toluene / 18 h / 90 °C

5: H₂; NH₃ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

6: 89 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ammonia; hydrogen; potassium hexamethylsilazane; potassium carbonate; sodium t-butanolate; DavePhos; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; ethanol; toluene; acetonitrile; xylene; 2: Wittig reaction;

DOI:10.1021/ol0344570

Reference yield:

2-bromo-4-methoxybenzaldehyde (43192-31-0) → 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester (557056-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / KN(TMS)2 / tetrahydrofuran; toluene / 4 h

2: 87 percent / H₂ / Pd/C / ethanol / 2 h / 760 Torr

3: 73 percent / sodium tert-butoxide; 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; tris(dibenzylideneacetone)dipalladium / toluene / 18 h / 90 °C

4: H₂; NH₃ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

5: 89 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ammonia; hydrogen; potassium hexamethylsilazane; potassium carbonate; sodium t-butanolate; DavePhos; palladium on activated charcoal; Rh/Al₂O₃; In tetrahydrofuran; ethanol; toluene; acetonitrile; 1: Wittig reaction;

DOI:10.1021/ol0344570

Reference yield:

7-(2-bromo-4-methoxyphenyl)hept-6-enenitrile (557056-02-7) → 4-{2-[7-(bis-tert-butoxycarbonylmethyl-amino)heptyl]-5-methoxyphenyl}piperazine-1-carboxylic acid tert-butyl ester (557056-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / H₂ / Pd/C / ethanol / 2 h / 760 Torr

2: 73 percent / sodium tert-butoxide; 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; tris(dibenzylideneacetone)dipalladium / toluene / 18 h / 90 °C

3: H₂; NH₃ / Rh/Al₂O₃ / ethanol / 5 h / 760 Torr

4: 89 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; ammonia; hydrogen; potassium carbonate; sodium t-butanolate; DavePhos; palladium on activated charcoal; Rh/Al₂O₃; In ethanol; toluene; acetonitrile;

DOI:10.1021/ol0344570

upstream raw materials:

bromoacetic acid tert-butyl ester

6-bromo-1-hexanenitrile

2-bromo-4-methoxybenzaldehyde

7-(2-bromo-4-methoxyphenyl)hept-6-enenitrile

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