(1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile

Base Information

• Chemical Name: (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile
• CAS No.: 1415118-36-3
• Molecular Formula: C₂₀H₂₁NO
• Molecular Weight: 291.393
• Mol file: 1415118-36-3.mol

Synonyms:(1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile

Chemical Property of (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile

There total 5 articles about (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile 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: 45.0%

(4-methylphenyl)acetonitrile (2947-61-7) + (S)-(((1,4-diiodobutan-2-yl)oxy)methyl)benzene (554427-73-5) → (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile (1415118-36-3) + (1R,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile (1415118-41-0)

Guidance literature:

(4-methylphenyl)acetonitrile; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

(S)-(((1,4-diiodobutan-2-yl)oxy)methyl)benzene; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12.3333h;

DOI:10.1016/j.tetasy.2012.10.004 DOI:10.1016/j.tetasy.2012.10.004

Reference yield:

dimethyl (S)-(-)-2-benzyloxybutanedioate (82130-73-2) → (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile (1415118-36-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; calcium chloride / ethanol / 2.5 h / 0 °C

2.1: triethylamine / dichloromethane / 6 h / 0 °C / Inert atmosphere

3.1: sodium iodide / acetone / 4 h / 70 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

4.2: 12.33 h / 0 - 20 °C

With sodium tetrahydroborate; sodium hydride; triethylamine; sodium iodide; calcium chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetasy.2012.10.004 DOI:10.1016/j.tetasy.2012.10.004

Reference yield:

C13H20O7S2 (1185984-56-8) → (1S,3S)-3-(benzyloxy)-1-(p-tolyl)cyclopentanecarbonitrile (1415118-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide / acetone / 4 h / 70 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 12.33 h / 0 - 20 °C

With sodium hydride; sodium iodide; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetasy.2012.10.004 DOI:10.1016/j.tetasy.2012.10.004

upstream raw materials:

dimethyl (S)-(-)-2-benzyloxybutanedioate

(4-methylphenyl)acetonitrile

(S)-(((1,4-diiodobutan-2-yl)oxy)methyl)benzene

(2R)-2-phenylmethoxybutane-1,4-diol

Downstream raw materials:

1-((1R,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene

(R)-3-methyl-3-(p-tolyl)cyclopentan-1-one

Refernces

• 1、 Chavan, Subhash P.,Lasonkar, Pradeep B.. "A chiral pool based approach to antipodes of α-cuparenone". . p. 1496 - 1500. Retrieved 2013/01/15.