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

Base Information

• Chemical Name: methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclobutyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate
• CAS No.: 439919-81-0
• Molecular Formula: C₂₂H₂₇NO₄
• Molecular Weight: 369.461

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 8 articles about methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclobutyloxy)-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: 53.0%

cyclobutanol (2919-23-5) + methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate (752259-59-9) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclobutyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (439919-81-0)

Guidance literature:

With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

(3aR,7aS)-2-[3-(benzyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile (752259-56-6) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclobutyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (439919-81-0)

Guidance literature:

Multi-step reaction with 8 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: 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: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

5.2: tetrahydrofuran / 1 h / 0 °C

6.1: 8.82 g / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 20 °C

7.1: 26 percent / H₂ / Pd/C / methanol / 72 h / atmospheric pressure

8.1: 53 percent / PPh₃; ADDP / CH₂Cl₂ / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; sodium hydride; ozone; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Dieckmann condensation;

DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

(2s,3aR,6aS)-2-[3-(benzyloxy)-4-methoxyphenyl]-5-oxooctahydropentalene-2-carbonitrile (752259-58-8) → methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclobutyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (439919-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: tetrahydrofuran / 1 h / 0 °C

2.1: 8.82 g / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 20 °C

3.1: 26 percent / H₂ / Pd/C / methanol / 72 h / atmospheric pressure

4.1: 53 percent / PPh₃; ADDP / CH₂Cl₂ / 20 °C

With hydrogen; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2004.02.010

upstream raw materials:

cyclobutanol

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

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

(2s,3aR,6aS)-2-[3-(benzyloxy)-4-methoxyphenyl]-5-oxooctahydropentalene-2-carbonitrile

Downstream raw materials:

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

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