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

Base Information

• Chemical Name: 2-acetoxy-12-benzyl-12-aza-bicyclo[9.2.1]tetradeca-1⁽¹³⁾,11⁽¹⁴⁾-diene-3-carboxylic acid methyl ester
• CAS No.: 251347-10-1
• Molecular Formula: C₂₄H₃₁NO₄
• Molecular Weight: 397.514

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

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

Chemical Property:

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

There total 1 articles about 2-acetoxy-12-benzyl-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: 46.0%

acetic acid (64-19-7,77671-22-8) + benzylamine (100-46-9) + (Z)-3-Formyl-5-oxo-cyclododec-2-enecarboxylic acid methyl ester → (Z)-12-Benzyl-12-aza-bicyclo[9.2.1]tetradeca-1(13),2,11(14)-triene-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 (251347-10-1) + 12-benzyl-2-benzylamino-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene-3-carboxylic acid methyl ester

Guidance literature:

In tetrahydrofuran; at 65 ℃; for 1h;

DOI:10.1021/jo991022a

Reference yield: 91.0%

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

Guidance literature:

With sodium methylate; In methanol; 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-eth-(E)-ylidene-12-aza-bicyclo[9.2.1]tetradeca-1(13),11(14)-diene

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / NaOMe / methanol / 1.5 h / 20 °C

2.1: 63 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 91 percent / NaCl / dimethylsulfoxide; H₂O / 1.5 h / 180 - 190 °C

4.1: KH / dimethylsulfoxide

4.2: 73 percent / dimethylsulfoxide / 0.33 h / 20 °C

With tetrapropylammonium perruthennate; sodium methylate; potassium hydride; sodium chloride; In methanol; dichloromethane; water; dimethyl sulfoxide; 1.1: Deacetylation / 2.1: Oxidation / 3.1: Decarboxylation / 4.1: Dehydroiodination / 4.2: Condensation;

DOI:10.1021/jo991022a

upstream raw materials:

acetic acid

benzylamine

Downstream raw materials:

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

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

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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