(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

Base Information

Chemical Name:(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide
CAS No.:1557243-42-1
Molecular Formula:C₁₉H₂₀ClNO₂
Molecular Weight:329.826
Hs Code.:

Synonyms:(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

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Chemical Property of (1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

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Technology Process of (1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

There total 5 articles about (1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide 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: 97.0%

: 494846-26-3
(+)-trans-(1R,3R)-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid

: 95-03-4
5-chloro-2-methoxyaniline

: 1557243-42-1
(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

Guidance literature:: (+)-trans-(1R,3R)-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

5-chloro-2-methoxyaniline; With triethylamine; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/acsmedchemlett.9b00001

Reference yield:

: 50672-13-4,99647-69-5
(±)-trans-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid

: 1557243-42-1
(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; dihydrogen peroxide; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water;
DOI:10.1021/acsmedchemlett.9b00001

Reference yield:

: 4489-17-2,54864-31-2
(+/-)-2,2-dimethyl-3t-phenyl-cyclopropane-r-carbonyl chloride

: 1557243-42-1
(1R,3R)-N-(5-chloro-2-methoxyphenyl)-2,2-dimethyl-3-phenylcyclopropane-1-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; dihydrogen peroxide; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; dichloromethane; cyclohexane; water;
DOI:10.1021/acsmedchemlett.9b00001