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

Base Information

Chemical Name:methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate
CAS No.:752259-59-9
Molecular Formula:C₁₈H₂₁NO₄
Molecular Weight:315.369
Hs Code.:

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

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

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

There total 9 articles about methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-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: 26.0%

: methyl (3aRS,5RS,6aRS)-5-[3-(benzyloxy)-4-methoxyphenyl]-5-cyano-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate

: 752259-59-9
methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol;
DOI:10.1016/j.bmcl.2003.12.018

Reference yield:

: 752259-57-7
dimethyl 2,2'-[(1R,2S)-4-[3-(benzyloxy)-4-methoxyphenyl]-4-cyanocyclopentane-1,2-diyl]diacetate

: 752259-59-9
methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 48 percent / NaCl; H₂O / dimethylsulfoxide / 1 h / 165 °C

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

2.2: tetrahydrofuran / 1 h / 0 °C

3.1: 8.82 g / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 20 °C

4.1: 26 percent / H₂ / Pd/C / methanol / 72 h / atmospheric pressure

With hydrogen; sodium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1.1: Dieckmann condensation;
DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

: [(1R,2S)-4-(3-Benzyloxy-4-methoxy-phenyl)-2-carboxymethyl-4-cyano-cyclopentyl]-acetic acid

: 752259-59-9
methyl (2s,3aR,5r,6aS)-5-cyano-5-(3-hydroxy-4-methoxyphenyl)octahydropentalene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 0 °C

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

2.2: 48 percent / NaCl; H₂O / dimethylsulfoxide / 1 h / 165 °C

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

3.2: tetrahydrofuran / 1 h / 0 °C

4.1: 8.82 g / PPh₃; Et₃N / Pd(OAc)2 / dimethylformamide / 20 °C

5.1: 26 percent / H₂ / Pd/C / methanol / 72 h / atmospheric pressure

With hydrogen; sodium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide; 2.1: Dieckmann condensation;
DOI:10.1016/j.ejmech.2004.02.010