cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

Base Information

Chemical Name:cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol
CAS No.:1432097-55-6
Molecular Formula:C₁₈H₁₈F₃NO₃
Molecular Weight:353.341
Hs Code.:

Synonyms:cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

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Chemical Property of cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

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Technology Process of cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

There total 11 articles about cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol 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: 47.0%

: 1432048-90-2
(S)-3-[hydroxy(pyridin-2-yl)methyl]-3-[4-(trifluoromethoxy)phenyl]-cyclobutanone

: 917-54-4
methyllithium

: 1432097-59-0
trans-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)phenyl]cyclobutanol

: 1432097-55-6
cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

Guidance literature:: In tetrahydrofuran; diethyl ether; at 0 ℃; Cooling with acetone-dry ice;

Reference yield:

: 49561-96-8
(4-trifluoromethoxy-phenyl)-acetonitrile

: 1432097-55-6
cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium t-butanolate / dimethyl sulfoxide; water / 20 - 125 °C

2.1: methanol / 20 - 70 °C

3.1: n-butyllithium / hexane; diethyl ether / 0.67 h / -78 °C

3.2: -78 - 20 °C

4.1: formic acid; triethylamine; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II) / 192 h / 55 °C

5.1: diethyl ether; tetrahydrofuran / 0 °C / Cooling with acetone-dry ice

With methanol; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; formic acid; triethylamine; sodium t-butanolate; In tetrahydrofuran; diethyl ether; hexane; water; dimethyl sulfoxide;

Reference yield:

: 1432048-71-9
3-hydroxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile

: 1432097-55-6
cis-3-[(S)-hydroxy(pyridin-2-yl)methyl]-1-methyl-3-[4-(trifluoromethoxy)-phenyl]cyclobutanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux

1.2: 20 - 100 °C

2.1: n-butyllithium / hexane; diethyl ether / 0.75 h / Cooling with acetone-dry ice

2.2: 20 °C

3.1: methanol; sodium tetrahydroborate / 20 °C

4.1: hydrogenchloride / water; acetone / 20 °C

5.1: Chiralpak AD DAC column / Resolution of racemate

6.1: diethyl ether; tetrahydrofuran / 0 °C / Cooling with acetone-dry ice

With hydrogenchloride; methanol; sodium tetrahydroborate; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; water; acetone; toluene;