tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate
• CAS No.: 1416051-64-3
• Molecular Formula: C₂₆H₂₉NO₅S
• Molecular Weight: 467.586

Synonyms:tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate

There total 4 articles about tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate 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: 66.0%

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzo[b]thiophene-2-carboxylic acid (1416051-63-2) + benzyl alcohol (100-51-6,185532-71-2) → tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate (1416051-64-3)

Guidance literature:

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzo[b]thiophene-2-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 0.25h;

benzyl alcohol; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1021/jm301474t

Reference yield:

ethyl 3-hydroxybenzothiophene-2-carboxylate (5556-20-7) → tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate (1416051-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine / tetrahydrofuran / 0.33 h / Inert atmosphere

1.2: Mitsunobu Displacement / 1.58 h / 0 - 20 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / methanol / 3 h / 20 °C

3.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 0.25 h / 20 °C

3.2: 18 h / 20 °C

With lithium hydroxide monohydrate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile; 1.1: |Mitsunobu Displacement;

DOI:10.1021/jm301474t

Reference yield:

Methyl thiosalicylate (4892-02-8) → tert-butyl 4-((2-((benzyloxy)carbonyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate (1416051-64-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.28 h / 0 - 20 °C

2.1: triphenylphosphine / tetrahydrofuran / 0.33 h / Inert atmosphere

2.2: Mitsunobu Displacement / 1.58 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / methanol / 3 h / 20 °C

4.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 0.25 h / 20 °C

4.2: 18 h / 20 °C

With lithium hydroxide monohydrate; potassium tert-butylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile; 1.1: |Dieckmann Condensation / 2.1: |Mitsunobu Displacement;

DOI:10.1021/jm301474t

upstream raw materials:

Methyl thiosalicylate

3-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzo[b]thiophene-2-carboxylic acid

benzyl alcohol

ethyl 3-hydroxybenzothiophene-2-carboxylate

Downstream raw materials:

benzyl 3-(piperidin-4-yloxy)benzo[b]thiophene-2-carboxylate

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