methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

Base Information

Chemical Name:methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate
CAS No.:371247-45-9
Molecular Formula:C₁₄H₁₃ClN₂O₃
Molecular Weight:292.722
Hs Code.:

Synonyms:methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

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Chemical Property of methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

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Technology Process of methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

There total 9 articles about methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate 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%

: 371247-44-8
(5S,1R,3R,4R)-3-aza-4-(triethylsilyloxy)-6-(6-chloro(3-pyridyl))-5-(methoxycarbonyl)bicyclo[2.2.2]oct-2-en-2-yl (tert-butoxy)formate

: 371247-45-9
methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; for 14h;
DOI:10.1021/ol016420q

Reference yield:

: 1121-89-7
piperidine-2,6-dione

: 371247-45-9
methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Et₃N / diethyl ether / 0.17 h / 5 °C

2.1: Me₂AlCl / CH₂Cl₂; toluene / -78 °C

2.2: 79 percent / CH₂Cl₂; toluene / 0.25 h / -78 °C

3.1: 84 percent / Sm(OTf)3 / 12 h / 60 °C

4.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h

5.1: 81 percent / n-Bu₄NF; H₂O / tetrahydrofuran / 14 h

With dmap; tetrabutyl ammonium fluoride; water; dimethylaluminum chloride; triethylamine; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.2: hetero Dies-Alder reaction;
DOI:10.1021/ol016420q

Reference yield:

: 371247-41-5
2,6-bis(triethylsilyloxy)-3,4-dihydropyridine

: 371247-45-9
methyl (6S,5R)-6-(6-chloro(3-pyridyl))-5-cyano-2-hydroxycyclohex-1-ene-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Me₂AlCl / CH₂Cl₂; toluene / -78 °C

1.2: 79 percent / CH₂Cl₂; toluene / 0.25 h / -78 °C

2.1: 84 percent / Sm(OTf)3 / 12 h / 60 °C

3.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h

4.1: 81 percent / n-Bu₄NF; H₂O / tetrahydrofuran / 14 h

With dmap; tetrabutyl ammonium fluoride; water; dimethylaluminum chloride; triethylamine; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene; 1.2: hetero Dies-Alder reaction;
DOI:10.1021/ol016420q