(4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone

Base Information

• Chemical Name: (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone
• CAS No.: 1429122-63-3
• Molecular Formula: C₂₁H₂₀ClNO₂
• Molecular Weight: 353.848
• Mol file: 1429122-63-3.mol

Synonyms:(4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone

Chemical Property of (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone

There total 6 articles about (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone 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: 78.0%

tert-butyl 3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-ene-7-carboxylate (1429122-62-2) + 4-chloro-benzoyl chloride (122-01-0) → (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone (1429122-63-3)

Guidance literature:

tert-butyl 3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-ene-7-carboxylate; With trifluoroacetic acid; In dichloromethane; for 0.0833333h; Molecular sieve; Inert atmosphere;

4-chloro-benzoyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo400077m

Reference yield:

3-oxo-piperidine-1-carboxylic acid tert-butyl ester (98977-36-7) → (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone (1429122-63-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: zinc/copper couple / tetrahydrofuran; toluene / 0.17 h / 0 °C / Sonication; Inert atmosphere

1.2: Inert atmosphere

2.1: 3,5-dicholoropyridine N-oxide; methanesulfonic acid / 1,2-dichloro-ethane / Inert atmosphere

2.2: 4 h / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water / N,N-dimethyl-formamide / 1.83 h / 90 °C

5.1: trifluoroacetic acid / dichloromethane / 0.08 h / Molecular sieve; Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; 3,5-dicholoropyridine N-oxide; zinc/copper couple; water; caesium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4.1: |Suzuki Coupling;

DOI:10.1021/jo400077m

Reference yield:

tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)piperidine-1-carboxylate (1429121-56-1) → (4-chlorophenyl)(3-phenyl-1-oxa-7-azaspiro[4.5]dec-2-en-7-yl)methanone (1429122-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 3,5-dicholoropyridine N-oxide; methanesulfonic acid / 1,2-dichloro-ethane / Inert atmosphere

1.2: 4 h / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water / N,N-dimethyl-formamide / 1.83 h / 90 °C

4.1: trifluoroacetic acid / dichloromethane / 0.08 h / Molecular sieve; Inert atmosphere

4.2: 2 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; 3,5-dicholoropyridine N-oxide; water; caesium carbonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 3.1: |Suzuki Coupling;

DOI:10.1021/jo400077m

upstream raw materials:

tert-butyl 3-hydroxy-3-(prop-2-yn-1-yl)piperidine-1-carboxylate

3-oxo-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-oxo-1-oxa-7-azaspiro[4.5]decane-7-carboxylate

tert-butyl 3-{[(trifluoromethyl)sulfonyl]oxy}-1-oxa-7-azaspiro[4.5]dec-2-ene-7-carboxylate

Refernces