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

Base Information

Chemical Name:(2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid
CAS No.:439920-02-2
Molecular Formula:C₂₀H₂₂F₃NO₄
Molecular Weight:397.394
Hs Code.:

Synonyms:(2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

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Chemical Property of (2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

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Technology Process of (2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

There total 9 articles about (2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid 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: 79.0%

: 439919-87-6
methyl (2s,3aR,5r,6aS)-5-cyano-5-[4-methoxy-3-(3,3,3-trifluoropropoxy)phenyl]octahydropentalene-2-carboxylate

: 439920-02-2
(2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1h;
DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

: 752259-56-6
(3aR,7aS)-2-[3-(benzyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile

: 439920-02-2
(2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 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: 58 percent / PPh₃; ADDP / CH₂Cl₂ / 20 °C

9.1: 79 percent / aq. NaOH / methanol; tetrahydrofuran / 1 h / 20 °C

With sodium hydroxide; 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:

: 752259-58-8
(2s,3aR,6aS)-2-[3-(benzyloxy)-4-methoxyphenyl]-5-oxooctahydropentalene-2-carbonitrile

: 439920-02-2
(2S,3aS,5R,6aR)-5-Cyano-5-[4-methoxy-3-(3,3,3-trifluoro-propoxy)-phenyl]-octahydro-pentalene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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: 58 percent / PPh₃; ADDP / CH₂Cl₂ / 20 °C

5.1: 79 percent / aq. NaOH / methanol; tetrahydrofuran / 1 h / 20 °C

With sodium hydroxide; 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