(2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide

Base Information

• Chemical Name: (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide
• CAS No.: 828919-04-6
• Molecular Formula: C₂₆H₃₆N₂O₅
• Molecular Weight: 456.582
• Mol file: 828919-04-6.mol

Synonyms:(2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide

Chemical Property of (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide

There total 9 articles about (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide 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:

O-2-methoxypropane 2-hydroxylamine (103491-33-4) + (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (440103-32-2) → (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide (828919-04-6)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.12.018

Reference yield:

methyl (2s,3aR,5r,6aS)-5-cyano-5-[3-(cyclopentyloxy)-4-methoxyphenyl]octahydropentalene-2-carboxylate (440103-33-3) → (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide (828919-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / aq. KOH / methanol; tetrahydrofuran / 4 h / 20 °C

2: 453 mg / EDC*HCl; HOBt / dimethylformamide / 2 h / 20 °C

With potassium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2004.02.010

Reference yield:

(3aR,7aS)-2-[3-(cyclopentyloxy)-4-methoxyphenyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carbonitrile (752259-53-3) → (2S,3aS,5R,6aR)-5-Cyano-5-(3-cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid (1-methoxy-1-methyl-ethoxy)-amide (828919-04-6)

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

5.2: 37 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: 108 mg / diethyl ether; tetrahydrofuran / 0 °C

8.1: 75 percent / aq. KOH / methanol; tetrahydrofuran / 4 h / 20 °C

9.1: 453 mg / EDC*HCl; HOBt / dimethylformamide / 2 h / 20 °C

With potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; dihydrogen peroxide; sodium hydride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 4.1: Dieckmann condensation;

DOI:10.1016/j.ejmech.2004.02.010

upstream raw materials:

O-2-methoxypropane 2-hydroxylamine

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

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

(3S,4R)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3,4-bis-(2-oxo-ethyl)-cyclopentanecarbonitrile