tert-butyl cyclohexyl(4-methoxybenzyl)carbamate

Base Information

• Chemical Name: tert-butyl cyclohexyl(4-methoxybenzyl)carbamate
• CAS No.: 1396518-01-6
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• Mol file: 1396518-01-6.mol

Synonyms:tert-butyl cyclohexyl(4-methoxybenzyl)carbamate

Chemical Property of tert-butyl cyclohexyl(4-methoxybenzyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl cyclohexyl(4-methoxybenzyl)carbamate

There total 6 articles about tert-butyl cyclohexyl(4-methoxybenzyl)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: 87.0%

tert-butyl cyclohexyl(methyl)carbamate + 1-bromo-4-methoxy-benzene (104-92-7) → tert-butyl cyclohexyl(4-methoxybenzyl)carbamate (1396518-01-6)

Guidance literature:

tert-butyl cyclohexyl(methyl)carbamate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -60 ℃; for 1h; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at -60 - 20 ℃; for 1.5h; Inert atmosphere;

1-bromo-4-methoxy-benzene; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; PtBu₃*HBF₄; In toluene; at 25 ℃; for 17h; Inert atmosphere;

DOI:10.1002/anie.201310904

Reference yield: 69.0%

4-chloromethoxybenzene (623-12-1) + potassium tert-butyl cyclohexyl{(trifluoroborato)methyl}carbamate (1397275-19-2) → tert-butyl cyclohexyl(4-methoxybenzyl)carbamate (1396518-01-6)

Guidance literature:

With chloro (2-dicyclohexylphosphino-2 ‘,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II); caesium carbonate; In water; toluene; at 85 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol301955s

Reference yield:

tert-butyl cyclohexyl{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl}carbamate (1396514-87-6) → tert-butyl cyclohexyl(4-methoxybenzyl)carbamate (1396518-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydrogen difluoride / acetone; water / 0.5 h / 0 - 20 °C

2: chloro (2-dicyclohexylphosphino-2 ‘,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II); caesium carbonate / water; toluene / 3 h / 85 °C / Inert atmosphere

With potassium hydrogen difluoride; chloro (2-dicyclohexylphosphino-2 ‘,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II); caesium carbonate; In water; acetone; toluene; 2: |Suzuki-Miyaura Coupling;

DOI:10.1021/ol301955s

upstream raw materials:

4-chloromethoxybenzene

potassium tert-butyl cyclohexyl{(trifluoroborato)methyl}carbamate

tert-butyl cyclohexylcarbamate

tert-butyl cyclohexyl{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl}carbamate

Refernces

• 1、 Molander, Gary A.,Shin, Inji. "Potassium Boc-protected secondary aminomethyltrifluoroborates: Synthesis and Suzuki-Miyaura cross-coupling reactions". supporting information. p. 4458 - 4461. Retrieved 2012/10/30.