(4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene

Base Information

• Chemical Name: (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene
• CAS No.: 908149-96-2
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 908149-96-2.mol

Synonyms:(4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene

Chemical Property of (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene

There total 7 articles about (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene 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: 65.0%

Oxalic acid (5R,6R,9S)-9-acetoxy-1-[2-(3,4-dimethoxy-phenyl)-acetyl]-1-aza-spiro[4.4]non-7-en-6-yl ester methyl ester (908150-04-9) → (1S,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-ene (908149-95-1) + (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene (908149-96-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 2h;

DOI:10.1016/j.tet.2006.05.045

Reference yield:

Acetic acid (5S,6S,9R)-9-hydroxy-1-aza-spiro[4.4]non-7-en-6-yl ester (908149-93-9) → (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene (908149-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / triethylamine / acetonitrile / 1.17 h / -40 °C

2: DMAP / CH₂Cl₂ / 96 h / 20 °C

3: 65 percent / AIBN; n-Bu₃SnH / toluene / 2 h / 100 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/j.tet.2006.05.045

Reference yield:

1,4-diacetoxy-6-azaspiro[4.4]non-2-ene (908149-92-8) → (4S,5S)-N-(3,4-dimethoxyphenylacetyl)-4-acetoxy-6-azaspiro[4.4]non-1-ene (908149-96-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium azide; lyophilized electric eel acetyl cholinesterase; sodium dihydrogen phosphate / pH 6.9

2: 80 percent / triethylamine / acetonitrile / 1.17 h / -40 °C

3: DMAP / CH₂Cl₂ / 96 h / 20 °C

4: 65 percent / AIBN; n-Bu₃SnH / toluene / 2 h / 100 °C

With dmap; sodium azide; sodium dihydrogen phosphate; 2,2'-azobis(isobutyronitrile); lyophilized electric eel acetyl cholinesterase; tri-n-butyl-tin hydride; triethylamine; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/j.tet.2006.05.045

upstream raw materials:

Oxalic acid (5R,6R,9S)-9-acetoxy-1-[2-(3,4-dimethoxy-phenyl)-acetyl]-1-aza-spiro[4.4]non-7-en-6-yl ester methyl ester

Acetic acid (5S,6S,9R)-9-hydroxy-1-aza-spiro[4.4]non-7-en-6-yl ester

1,4-diacetoxy-6-azaspiro[4.4]non-2-ene

(5R,6R,9S)-6,9-Diacetoxy-1-aza-spiro[4.4]non-7-ene-1-carboxylic acid tert-butyl ester

Downstream raw materials:

2-(3,4-Dimethoxy-phenyl)-1-((5S,6S)-6-hydroxy-1-aza-spiro[4.4]non-7-en-1-yl)-ethanone

(S)-1-[2-(3,4-Dimethoxy-phenyl)-acetyl]-1-aza-spiro[4.4]non-7-en-6-one

(S)-1-[2-(3,4-Dimethoxy-phenyl)-acetyl]-1-aza-spiro[4.4]non-8-en-6-one

2-(3,4-Dimethoxy-phenyl)-1-((5S,9S)-9-hydroxy-1-aza-spiro[4.4]non-6-en-1-yl)-ethanone