3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

Base Information

Chemical Name:3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone
CAS No.:1432051-45-0
Molecular Formula:C₁₆H₁₃F₃N₂O₂
Molecular Weight:322.287
Hs Code.:

Synonyms:3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

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Chemical Property of 3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

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Technology Process of 3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

There total 4 articles about 3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone 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:

: 20249-16-5
3-oxo-cyclobutanecarbonitrile

: 1432051-45-0
3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C / Dean-Stark; Reflux

2.1: potassium hexamethylsilazane / toluene / 4 h / 60 °C

3.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C

3.2: 2 h / -78 °C

4.1: water; hydrogenchloride / diethyl ether; hexane / 0.5 h / -78 - 20 °C

5.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 20 °C

6.1: water; hydrogenchloride / acetone / 16 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; water; potassium hexamethylsilazane; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; dichloromethane; acetone; toluene;
DOI:10.1021/acs.jmedchem.6b00287

Reference yield:

: 20249-16-5
3-oxo-cyclobutanecarbonitrile

: 1432051-45-0
3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

: 1432051-52-9
3-[(R)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C / Reflux

2.1: potassium hexamethylsilazane / toluene / 4 h / 60 °C

3.1: n-butyllithium / diethyl ether / 1 h / -78 °C

3.2: 2 h / -78 °C

3.3: 0.5 h / -78 - 20 °C

4.1: methanol; sodium tetrahydroborate / dichloromethane / 1 h / 20 °C

5.1: hydrogenchloride / acetone / 20 °C

6.1: chiral column Column: AD-H / Resolution of racemate

With hydrogenchloride; methanol; sodium tetrahydroborate; n-butyllithium; potassium hexamethylsilazane; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; acetone; toluene;

Reference yield:

: 15760-35-7
3-methylenecyclobutanecarbonitrile

: 1432051-45-0
3-[(S)-hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethyl)pyridin-2-yl]-cyclobutanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium periodate; ruthenium(III) chloride trihydrate / dichloromethane; water; acetonitrile / 1.5 h / 0 - 10 °C

2.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C / Dean-Stark; Reflux

3.1: potassium hexamethylsilazane / toluene / 4 h / 60 °C

4.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C

4.2: 2 h / -78 °C

5.1: water; hydrogenchloride / diethyl ether; hexane / 0.5 h / -78 - 20 °C

6.1: sodium tetrahydroborate / methanol; dichloromethane / 3 h / 20 °C

7.1: water; hydrogenchloride / acetone / 16 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; ruthenium(III) chloride trihydrate; water; potassium hexamethylsilazane; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1021/acs.jmedchem.6b00287