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

Base Information

Chemical Name:methyl (2r,3aR,5s,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate
CAS No.:440103-34-4
Molecular Formula:C₂₃H₂₉NO₄
Molecular Weight:383.488
Hs Code.:

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

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

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

There total 8 articles about methyl (2r,3aR,5s,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: 35.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 439919-55-8
(2r,3aR,6aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-(1,3-dithian-2-ylidene)octahydropentalene-2-carbonitrile

: 440103-34-4
methyl (2r,3aR,5s,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

: 440103-35-5
methyl (2s,3aR,5s,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

Guidance literature:: (2r,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:

: 752259-53-3
(3aR,7aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile

: 440103-34-4
methyl (2r,3aR,5s,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

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

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

5.2: 42 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: 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:

: 440103-31-1
(2r,3aR,6aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-oxooctahydropentalene-2-carbonitrile

: 440103-34-4
methyl (2r,3aR,5s,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 42 percent / tetrahydrofuran; hexane / -78 - 0 °C

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

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

3.1: diethyl ether; tetrahydrofuran / 0 °C

With n-butyllithium; dihydrogen peroxide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; hexane; water; acetonitrile;
DOI:10.1016/j.ejmech.2004.02.010