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

Base Information

• Chemical Name: 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene
• CAS No.: 1415118-43-2
• Molecular Formula: C₂₀H₂₄O
• Molecular Weight: 280.41
• Mol file: 1415118-43-2.mol

Synonyms:1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene

Chemical Property of 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene

There total 8 articles about 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene 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:

C20H22O2 → 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene (1415118-43-2)

Guidance literature:

With hydrazine hydrate; sodium hydroxide; In ethylene glycol; at 180 ℃; for 24h;

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) → 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene (1415118-43-2)

Guidance literature:

Multi-step reaction with 6 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

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

6.1: hydrazine hydrate; sodium hydroxide / ethylene glycol / 24 h / 180 °C

With sodium tetrahydroborate; sodium hydride; diisobutylaluminium hydride; hydrazine hydrate; triethylamine; sodium iodide; calcium chloride; sodium hydroxide; In ethanol; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; acetone; toluene;

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

Reference yield:

(S)-(((1,4-diiodobutan-2-yl)oxy)methyl)benzene (554427-73-5) → 1-((1S,3S)-3-(benzyloxy)-1-methylcyclopentyl)-4-methylbenzene (1415118-43-2)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 12.33 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

3.1: hydrazine hydrate; sodium hydroxide / ethylene glycol / 24 h / 180 °C

With sodium hydride; diisobutylaluminium hydride; hydrazine hydrate; sodium hydroxide; In dichloromethane; ethylene glycol; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

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

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

(4-methylphenyl)acetonitrile

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

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.