2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

Base Information

• Chemical Name: 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile
• CAS No.: 1610033-07-2
• Molecular Formula: C₂₀H₁₉F₃N₂O
• Molecular Weight: 360.379

Synonyms:2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

Chemical Property of 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

There total 11 articles about 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile 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:

(R)-2-benzyl 1-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate → 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile (1610033-07-2)

Guidance literature:

Multi-step reaction with 10 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: pyridine; thionyl chloride / 0.75 h / 0 - 110 °C / Inert atmosphere

3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr

4: 4-methyl-morpholine / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere

5: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C

6: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere

7: ethanol / 20 °C / Inert atmosphere

8: sodium hydroxide; copper(l) iodide / butan-1-ol / 90 °C / Inert atmosphere

9: triethylamine / 0 - 20 °C / Inert atmosphere

10: dimethyl sulfoxide / 9 h / 40 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; thionyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; dimethyl sulfoxide; butan-1-ol;

DOI:10.1021/acs.jmedchem.7b00982

Reference yield:

((2R,4R)-4-(trifluoromethyl)pyrrolidin-2-yl)methanol hydrochloride → 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile (1610033-07-2)

Guidance literature:

Multi-step reaction with 4 steps

1: ethanol / 20 °C / Inert atmosphere

2: sodium hydroxide; copper(l) iodide / butan-1-ol / 90 °C / Inert atmosphere

3: triethylamine / 0 - 20 °C / Inert atmosphere

4: dimethyl sulfoxide / 9 h / 40 °C / Inert atmosphere

With copper(l) iodide; triethylamine; sodium hydroxide; In ethanol; dimethyl sulfoxide; butan-1-ol;

DOI:10.1021/acs.jmedchem.7b00982

Reference yield:

(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride (77449-94-6,441067-49-8) → 2-((2R,4R)-1-(4-(benzyloxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile (1610033-07-2)

Guidance literature:

Multi-step reaction with 13 steps

1: sodium hydroxide / tetrahydrofuran; water / 13 h / 25 °C

2: triethylamine / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

3: chromium(VI) oxide; sulfuric acid / water; acetone / 1.17 h / 10 - 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5: pyridine; thionyl chloride / 0.75 h / 0 - 110 °C / Inert atmosphere

6: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr

7: 4-methyl-morpholine / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere

8: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C

9: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere

10: ethanol / 20 °C / Inert atmosphere

11: sodium hydroxide; copper(l) iodide / butan-1-ol / 90 °C / Inert atmosphere

12: triethylamine / 0 - 20 °C / Inert atmosphere

13: dimethyl sulfoxide / 9 h / 40 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; thionyl chloride; sulfuric acid; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; dimethyl sulfoxide; acetone; butan-1-ol;

DOI:10.1021/acs.jmedchem.7b00982

upstream raw materials:

(2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

2-benzyl 1-(tert-butyl) (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

(2R)-2-benzyl 1-tert-butyl 4-hydroxy-4-(trifluoromethyl) pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

methyl 2-((2R,4R)-1-(4-((1-(2-fluoro-5-methoxyphenyl)piperidin-4-yl)oxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetate

methyl 2-((2R,4R)-1-(4-hydroxyphenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetate

2-((2R,4R)-1-(4-hydroxyphenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

2-((2R,4R)-1-(4-(((3,4-trans)-1-(5-chloro-2-methoxypyridin-4-yl)-3-methylpiperidin-4-yl)oxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile

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