3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid

Base Information

• Chemical Name: 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid
• CAS No.: 204187-82-6
• Molecular Formula: C₂₈H₃₃NO₄S
• Molecular Weight: 479.64

Synonyms:3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid

Chemical Property of 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid

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Technology Process of 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid

There total 7 articles about 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12⁽¹⁵⁾-diene-3-carboxylic acid 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: 70.0%

benzylamine (100-46-9) + (Z)-12-Benzenesulfonyl-14-oxa-bicyclo[10.3.1]hexadec-1-ene-3,13-dione (204187-81-5) → 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1(14),12(15)-diene-3-carboxylic acid (204187-82-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 35 ℃; for 1.5h;

DOI:10.1021/ja973846k

Reference yield:

9-bromononan-1-ol (55362-80-6) → 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1(14),12(15)-diene-3-carboxylic acid (204187-82-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / Dess-Martin periodinane

2: tetrahydrofuran / -78 - 20 °C

3: 68 percent / KH / dimethylformamide / 20 °C

4: 85 percent / Pd(PPh₃)4; dppe / tetrahydrofuran / 6 h / Heating

5: 63 percent / TBAF; NH₄F / tetrahydrofuran / 20 °C

6: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7: 70 percent / Pd(PPh₃)4 / tetrahydrofuran / 35 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; potassium hydride; Dess-Martin periodane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Oxidation / 2: Cycloaddition / 3: Alkylation / 4: Cyclization / 5: desilylation / 6: Oxidation / 7: Cyclization;

DOI:10.1021/ja963795b

Reference yield:

{2-[3-(8-bromooctyl)oxiranyl]allyloxy}-tert-butyldimethylsilane (187808-10-2) → 3-Benzenesulfonyl-13-benzyl-13-aza-bicyclo[10.2.1]pentadeca-1(14),12(15)-diene-3-carboxylic acid (204187-82-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / KH / dimethylformamide / 20 °C

2: 85 percent / Pd(PPh₃)4; dppe / tetrahydrofuran / 6 h / Heating

3: 63 percent / TBAF; NH₄F / tetrahydrofuran / 20 °C

4: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5: 70 percent / Pd(PPh₃)4 / tetrahydrofuran / 35 °C

With ammonium fluoride; tetrabutyl ammonium fluoride; potassium hydride; Dess-Martin periodane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Cyclization / 3: desilylation / 4: Oxidation / 5: Cyclization;

DOI:10.1021/ja963795b

upstream raw materials:

benzylamine

(Z)-12-Benzenesulfonyl-14-oxa-bicyclo[10.3.1]hexadec-1-ene-3,13-dione

9-bromononan-1-ol

9-bromononanal

Downstream raw materials:

12-Benzenesulfonyl-2-benzyl-2-aza-tricyclo[10.2.1.1^3,14]hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾-dien-15-one

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