(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

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Chemical Name:(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate
CAS No.:1370320-06-1
Molecular Formula:C₁₆H₂₁ClN₂O₃
Molecular Weight:324.807
Hs Code.:

Synonyms:(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

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Chemical Property of (+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

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Technology Process of (+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

There total 8 articles about (+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate 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: 95.0%

: 1370320-05-0
(+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate

: 1370320-06-1
(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1039/c2ob06904k

Reference yield:

: 108-86-1,52753-63-6
bromobenzene

: 1370320-06-1
(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: dioxygenase from pseudomonas putida

2.1: hydrogen / methanol / 2 h / 20 °C / 1125.11 Torr

3.1: pyridine / 12 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 0.5 h / 0 °C

5.1: water / methanol; diethyl ether / 5 h / 20 °C / Alkaline conditions

6.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 2.5 h / -10 °C

6.2: 16 h / 20 °C

7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / ethanol; water; toluene / 5 h / 100 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; carbon tetrabromide; dioxygenase from pseudomonas putida; tetrabutyl ammonium fluoride; water; hydrogen; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; 7.1: |Suzuki Coupling;
DOI:10.1039/c2ob06904k

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 1370320-06-1
(+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogen / methanol / 2 h / 20 °C / 1125.11 Torr

2.1: pyridine / 12 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 0.5 h / 0 °C

4.1: water / methanol; diethyl ether / 5 h / 20 °C / Alkaline conditions

5.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 2.5 h / -10 °C

5.2: 16 h / 20 °C

6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / ethanol; water; toluene / 5 h / 100 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; water; hydrogen; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; 6.1: |Suzuki Coupling;
DOI:10.1039/c2ob06904k