2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile

Base Information

• Chemical Name: 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile
• CAS No.: 1352074-69-1
• Molecular Formula: C₂₃H₂₂Cl₂N₂O
• Molecular Weight: 413.346

Synonyms:2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile

Chemical Property of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile

There total 14 articles about 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile 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: 93.0%

2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetamide (1352063-00-3) → 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile (1352074-69-1)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm300354j

Reference yield:

C19H20Cl2O5S → 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile (1352074-69-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium azide / N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere

2.1: trimethylphosphane / tetrahydrofuran; water / 1 h / 25 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / methanol; water / Inert atmosphere; Reflux

4.1: Chiralcel OD-H / hexane; isopropyl alcohol / Resolution of racemate

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere

5.2: 5 h / 0 - 25 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

7.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 3 h / 25 °C / Inert atmosphere

8.1: thionyl chloride / 0 - 25 °C / Inert atmosphere

9.1: ammonia / methanol / 120 h / 25 °C / Inert atmosphere; Sealed tube

9.2: 72 h / 50 °C / Inert atmosphere; Sealed tube

10.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With sodium periodate; thionyl chloride; sodium azide; ruthenium(III) trichloride hydrate; ammonia; sodium hydride; sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; trimethylphosphane; In tetrahydrofuran; methanol; tetrachloromethane; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil;

DOI:10.1021/jm300354j

Reference yield:

(+/-)-(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one → 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetonitrile (1352074-69-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Chiralcel OD-H / hexane; isopropyl alcohol / Resolution of racemate

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere

2.2: 5 h / 0 - 25 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

4.1: sodium periodate; ruthenium(III) trichloride hydrate / tetrachloromethane; water; acetonitrile / 3 h / 25 °C / Inert atmosphere

5.1: thionyl chloride / 0 - 25 °C / Inert atmosphere

6.1: ammonia / methanol / 120 h / 25 °C / Inert atmosphere; Sealed tube

6.2: 72 h / 50 °C / Inert atmosphere; Sealed tube

7.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With sodium periodate; thionyl chloride; ruthenium(III) trichloride hydrate; ammonia; sodium hydride; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; mineral oil;

DOI:10.1021/jm300354j

upstream raw materials:

(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one

(5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)piperidin-2-one

(3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)piperidin-2-one

2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxopiperidin-3-yl)acetic acid

Downstream raw materials:

(3R,5R,6S)-3-((1H-tetrazol-5-yl)methyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)piperidin-2-one

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