methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

Base Information

Chemical Name:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate
CAS No.:1314795-23-7
Molecular Formula:C₂₇H₃₇NO₄S
Molecular Weight:471.661
Hs Code.:

Synonyms:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

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Chemical Property of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

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Technology Process of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

There total 9 articles about methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate 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: 61.0%

: 1026785-67-0
5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester

: 5034-06-0
trimethyl sulfoxonium chloride

: 1314795-23-7
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

Guidance literature:: trimethyl sulfoxonium chloride; With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 0.25h;

5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at 20 ℃; for 3h;
DOI:10.1021/jm401420j

Reference yield:

: 934-67-8,4331-54-8,13064-83-0
trans-4-methylcyclohexanecarboxylic acid

: 1314795-23-7
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dichloromethane; N,N-dimethyl-formamide / 3 h / 0 - 20 °C

2.1: pyridine / toluene / 16 h / Reflux

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

3.2: 3 h / -78 °C

4.1: copper(l) iodide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 40 °C

6.1: sodium hydride / dimethyl sulfoxide / 0.25 h / 20 °C

6.2: 3 h / 20 °C

With pyridine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; n-butyllithium; sodium hydride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm401420j

Reference yield:

: 55930-23-9
trans-4-methylcyclohexanecarbonyl chloride

: 1314795-23-7
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1r,4r)-4-methyl-N-(1-oxaspiro[2.5]octan-6-yl)cyclohexanecarboxamido)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / toluene / 16 h / Reflux

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C

2.2: 3 h / -78 °C

3.1: copper(l) iodide; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 40 °C

5.1: sodium hydride / dimethyl sulfoxide / 0.25 h / 20 °C

5.2: 3 h / 20 °C

With pyridine; hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; n-butyllithium; sodium hydride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm401420j