(1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol

Base Information

• Chemical Name: (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol
• CAS No.: 908149-94-0
• Molecular Formula: C₂₀H₂₅NO₆
• Molecular Weight: 375.422
• Mol file: 908149-94-0.mol

Synonyms:

Chemical Property of (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol

There total 3 articles about (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol 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:

1,4-diacetoxy-6-azaspiro[4.4]non-2-ene (908149-92-8) → (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol (908149-94-0)

Guidance literature:

Multi-step reaction with 2 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

With sodium azide; sodium dihydrogen phosphate; lyophilized electric eel acetyl cholinesterase; triethylamine; In acetonitrile;

DOI:10.1016/j.tet.2006.05.045

Reference yield:

N-Boc-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol → (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol (908149-94-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / DMAP; pyridine / CH₂Cl₂ / 12 h / 20 °C

2: 85 percent / TFA / CH₂Cl₂ / 20 °C

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

4: 80 percent / triethylamine / acetonitrile / 1.17 h / -40 °C

With pyridine; dmap; sodium azide; sodium dihydrogen phosphate; lyophilized electric eel acetyl cholinesterase; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2006.05.045

Reference yield:

(5R,6R,9S)-6,9-Diacetoxy-1-aza-spiro[4.4]non-7-ene-1-carboxylic acid tert-butyl ester (908150-03-8) → (1S,4R,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-en-4-ol (908149-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / TFA / CH₂Cl₂ / 20 °C

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

3: 80 percent / triethylamine / acetonitrile / 1.17 h / -40 °C

With sodium azide; sodium dihydrogen phosphate; lyophilized electric eel acetyl cholinesterase; triethylamine; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2006.05.045

upstream raw materials:

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:

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

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

(1S,5S)-N-(3,4-dimethoxyphenylacetyl)-1-acetoxy-6-azaspiro[4.4]non-2-ene

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