[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

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Chemical Name:[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester
CAS No.:183545-12-2
Molecular Formula:C₁₆H₂₃ClN₂O₃
Molecular Weight:326.823
Hs Code.:

Synonyms:[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

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Chemical Property of [(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

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Technology Process of [(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

There total 7 articles about [(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester 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: 67.0%

: 183545-09-7
[(1S,3R)-3-(6-Chloro-pyridin-3-yl)-4-oxo-cyclohexyl]-carbamic acid tert-butyl ester

: [(1S,3R,4R)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

: 183545-12-2
[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃;
DOI:10.1016/0040-4039(96)01739-X

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 183545-12-2
[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

2: 1.) K₂CO₃; 2.) Dess-Martin periodinane / 1.) CH₃OH, r. t.; 2.) CH₂Cl₂, r. t.

3: 80 percent / Br₂, (C₂H₅)3N / CH₂Cl₂ / 0 °C

4: (dba)3Pd*CHCl₃, Ph₃As / tetrahydrofuran / 55 °C

5: K-selectride / tetrahydrofuran / from -78 to 0 degC

6: 67 percent / NaBH₄ / methanol / 0 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; triphenyl-arsane; bromine; potassium tri-sec-butyl-borohydride; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0040-4039(96)01739-X

Reference yield:

: 77300-23-3,881832-47-9
cyclohex-(±)-(1R*,4S*)-2-ene-1,4-diyl dibenzoate

: 183545-12-2
[(1S,3R,4S)-3-(6-Chloro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

2: 1.) K₂CO₃; 2.) Dess-Martin periodinane / 1.) CH₃OH, r. t.; 2.) CH₂Cl₂, r. t.

3: 80 percent / Br₂, (C₂H₅)3N / CH₂Cl₂ / 0 °C

4: (dba)3Pd*CHCl₃, Ph₃As / tetrahydrofuran / 55 °C

5: K-selectride / tetrahydrofuran / from -78 to 0 degC

6: 67 percent / NaBH₄ / methanol / 0 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; triphenyl-arsane; bromine; potassium tri-sec-butyl-borohydride; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0040-4039(96)01739-X