(R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

Base Information

• Chemical Name: (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one
• CAS No.: 1579513-50-0
• Molecular Formula: C₂₆H₂₇N₃O₃
• Molecular Weight: 429.519
• Mol file: 1579513-50-0.mol

Synonyms:(R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

Chemical Property of (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

There total 6 articles about (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one 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: 36.0%

(R)-5-(4-bromophenyl)-6-((1-(cyclopropanecarbonyl) pyrrolidin-3-yl)methyl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579512-01-8) + (p-hydroxyphenyl)boronic acid (71597-85-8) → (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579513-50-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; for 3h; Inert atmosphere; Reflux;

Reference yield:

(R)-(+)-3-(hydroxymethyl)pyrrolidine (5082-74-6,85310-69-6,110013-18-8,110013-19-9) → (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579513-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C

2: triethylamine / 0 - 20 °C

3: caesium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C

4: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 3 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

4-bromo-N-(1-carbamoylcyclopropyl)benzamide → (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one (1579513-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 h / Heating

2: caesium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C

3: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 3 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; caesium carbonate; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2018.05.014

upstream raw materials:

(R)-5-(4-bromophenyl)-6-((1-(cyclopropanecarbonyl) pyrrolidin-3-yl)methyl)-4,6-diazaspiro[2.4]hept-4-en-7-one

(p-hydroxyphenyl)boronic acid

(R)-(+)-3-(hydroxymethyl)pyrrolidine

4-Bromobenzoic acid

Downstream raw materials:

(R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4'-(1-methyl-1H-pyrazol-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one

(R)-4'-(6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-5-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate