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

Base Information

Chemical Name:(2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid
CAS No.:440103-25-3
Molecular Formula:C₂₁H₂₈O₄
Molecular Weight:344.451
Hs Code.:

Synonyms:(2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

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Chemical Property of (2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

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Technology Process of (2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

There total 11 articles about (2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-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: 81.0%

: (3aRS,5SR,6aRS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylic acid

: 440103-25-3
(2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 4h; atmospheric pressure;
DOI:10.1016/j.bmc.2004.07.040

Reference yield:

: 440103-24-2
(3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2-pentalenone

: 440103-25-3
(2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: ZnI₂ / CH₂Cl₂ / 2 h / 20 °C

2: P(O)Cl₃; pyridine / 1.5 h / 120 °C

3: 93 percent / aq. KOH / ethane-1,2-diol / 4 h / 200 °C

4: 81 percent / H₂ / Pd/C / methanol / 4 h / atmospheric pressure

With pyridine; potassium hydroxide; hydrogen; zinc(II) iodide; trichlorophosphate; palladium on activated charcoal; In methanol; dichloromethane; ethylene glycol;
DOI:10.1016/j.bmc.2004.07.040

Reference yield:

: (3aRS,6aSR)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]-3,3a,4,6a-tetrahydro-2(1H)-pentalenone

: 440103-25-3
(2R,3aS,5R,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

2: 89 percent / H₂ / Ir(cod)py(PCy₃)PF₆ / CH₂Cl₂ / 1 h / atmospheric pressure

3: 92 percent / NMO; TPAP; MS₄A / CH₂Cl₂ / 24 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 2 h / 20 °C

5: P(O)Cl₃; pyridine / 1.5 h / 120 °C

6: 93 percent / aq. KOH / ethane-1,2-diol / 4 h / 200 °C

7: 81 percent / H₂ / Pd/C / methanol / 4 h / atmospheric pressure

With pyridine; potassium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; hydrogen; zinc(II) iodide; trichlorophosphate; palladium on activated charcoal; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethylene glycol;
DOI:10.1016/j.bmc.2004.07.040