(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

Base Information

Chemical Name:(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol
CAS No.:221649-23-6
Molecular Formula:C₁₂H₁₆ClNO₄S
Molecular Weight:305.782
Hs Code.:

Synonyms:(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

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Technology Process of (1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

There total 10 articles about (1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol 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: 88.0%

: 334700-58-2
(1R,2R,4S)-4-[(tert-Butyldimethylsilyl)oxy]-2-(2-chloro-5-pyridyl)-1-[(methylsulfonyl)oxy]cyclohexane

: 221649-23-6
(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1039/b002980g

Reference yield: 88.0%

: Methanesulfonic acid (1R,2S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-2-pyridin-3-yl-cyclohexyl ester

: 221649-23-6
(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)02354-5

Reference yield:

: 121651-99-8
(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one

: 221649-23-6
(1S,3R,4R)-3-(2-Chloro-5-pyridyl)-4-[(methylsulfonyl)oxy]cyclohexan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: K-Selectride / tetrahydrofuran / -78 °C

2: aq. NaOH / tetrahydrofuran / 0 °C

3: (i-Pr)2NEt, DMAP / CH₂Cl₂ / 0 - 20 °C

4: 82 percent / I₂, DMAP / pyridine; CCl₄ / 0 - 20 °C

5: 90 percent / Pd₂(dba)3*CHCl₃, triphenylarsine, CuI / tetrahydrofuran / 20 - 60 °C

6: 1.) K-Selectride; 2.) NaBH₄, CeCl₃*7H₂O / 1.) THF, -78 deg C; 2.) MeOH, 0 deg C

7: 99 percent / Et₃N / CH₂Cl₂ / 0 °C

8: 88 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; cerium(III) chloride; triphenyl-arsane; tetrabutyl ammonium fluoride; iodine; potassium tri-sec-butyl-borohydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane;
DOI:10.1016/S0040-4039(98)02354-5