methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

Base Information

• Chemical Name: methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate
• CAS No.: 440103-33-3
• Molecular Formula: C₂₃H₂₉NO₄
• Molecular Weight: 383.488

Synonyms:methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

Chemical Property of methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

There total 8 articles about methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate 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: 25.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2s,3aR,6aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-(1,3-dithian-2-ylidene)octahydropentalene-2-carbonitrile (752259-55-5) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (440103-33-3) + methyl (2r,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (439919-57-0)

Guidance literature:

(2s,3aR,6aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-(1,3-dithian-2-ylidene)octahydropentalene-2-carbonitrile; With dihydrogen peroxide; trifluoroacetic acid; In acetonitrile;

diazomethane; In diethyl ether;

DOI:10.1016/j.bmcl.2003.12.018

Reference yield:

(3aR,7aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile (752259-53-3) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (440103-33-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ozone / CH₂Cl₂ / 1 h / -78 °C

1.2: Ph₃P / CH₂Cl₂ / 1.5 h / -78 - 20 °C

2.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

3.1: 2.66 g / diethyl ether / 0 °C

4.1: NaH / 1,2-dimethoxy-ethane / 1.5 h / Heating

4.2: 48 percent / NaCl; H₂O / dimethylsulfoxide / 1 h / 165 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

5.2: 37 percent / tetrahydrofuran; hexane / -78 - 0 °C

6.1: TFA; H₂O₂ / acetonitrile; H₂O / 0.5 h / 80 °C

6.2: NaOH / acetonitrile; H₂O / 0.33 h / 40 °C

7.1: 108 mg / diethyl ether; tetrahydrofuran / 0 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; ozone; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 4.1: Dieckmann condensation;

DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

(3S,4R)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3,4-bis-(2-oxo-ethyl)-cyclopentanecarbonitrile (828919-77-3) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (440103-33-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

2.1: 2.66 g / diethyl ether / 0 °C

3.1: NaH / 1,2-dimethoxy-ethane / 1.5 h / Heating

3.2: 48 percent / NaCl; H₂O / dimethylsulfoxide / 1 h / 165 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

4.2: 37 percent / tetrahydrofuran; hexane / -78 - 0 °C

5.1: TFA; H₂O₂ / acetonitrile; H₂O / 0.5 h / 80 °C

5.2: NaOH / acetonitrile; H₂O / 0.33 h / 40 °C

6.1: 108 mg / diethyl ether; tetrahydrofuran / 0 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; water; acetonitrile; tert-butyl alcohol; 3.1: Dieckmann condensation;

DOI:10.1016/j.ejmech.2004.02.010

upstream raw materials:

diazomethane

(2s,3aR,6aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-(1,3-dithian-2-ylidene)octahydropentalene-2-carbonitrile

(3aR,7aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile

(3S,4R)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3,4-bis-(2-oxo-ethyl)-cyclopentanecarbonitrile

Downstream raw materials:

(2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

(2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide

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