12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

Base Information

• Chemical Name: 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester
• CAS No.: 251347-14-5
• Molecular Formula: C₂₂H₂₇NO₃
• Molecular Weight: 353.461

Synonyms:12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

Chemical Property of 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

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Technology Process of 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

There total 2 articles about 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl 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: 63.0%

12-benzyl-2-hydroxy-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester (251347-13-4) → 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester (251347-14-5)

Guidance literature:

With tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo991022a

Reference yield:

2-acetoxy-12-benzyl-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester (251347-10-1) → 12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester (251347-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaOMe / methanol / 1.5 h / 20 °C

2: 63 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

With tetrapropylammonium perruthennate; sodium methylate; In methanol; dichloromethane; 1: Deacetylation / 2: Oxidation;

DOI:10.1021/jo991022a

Reference yield: 91.0%

12-benzyl-2-oxo-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester (251347-14-5) → 12-benzyl-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-dien-2-one (251347-15-6)

Guidance literature:

With sodium chloride; In water; dimethyl sulfoxide; at 180 - 190 ℃; for 1.5h;

DOI:10.1021/jo991022a

upstream raw materials:

12-benzyl-2-hydroxy-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

2-acetoxy-12-benzyl-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester

Downstream raw materials:

12-benzyl-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-dien-2-one

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