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

Base Information

• Chemical Name: (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate
• CAS No.: 1370320-05-0
• Molecular Formula: C₂₂H₃₅ClN₂O₃Si
• Molecular Weight: 439.07

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-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: 93.0%

(+)-tert-butyl N-[(1R,4S)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]cyclohex-2-en-1-yl]carbamate (1370320-04-9) + 6-chloropyridin-3-ylboronic acid (444120-91-6) → (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate (1370320-05-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; water; toluene; at 100 ℃; for 5h; Inert atmosphere;

DOI:10.1039/c2ob06904k

Reference yield:

bromobenzene (108-86-1,52753-63-6) → (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate (1370320-05-0)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1039/c2ob06904k

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate (1370320-05-0)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1039/c2ob06904k

upstream raw materials:

(+)-tert-butyl N-[(1R,4S)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]cyclohex-2-en-1-yl]carbamate

6-chloropyridin-3-ylboronic acid

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

bromobenzene

Downstream raw materials:

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

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

N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide

(1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine

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