N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

Base Information

Chemical Name:N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide
CAS No.:827609-27-8
Molecular Formula:C₁₇H₁₉NO₂S
Molecular Weight:301.409
Hs Code.:

Synonyms:N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

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Chemical Property of N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

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Technology Process of N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

There total 7 articles about N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide 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: 77.0%

: 53881-34-8
2-isopropylbenzoic acid chloride

: 827609-21-2
cis-(5R,6R)-6-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-5-ol

: 827609-27-8
N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

Guidance literature:: With potassium hydrogencarbonate; In water; at 80 ℃; for 2.5h;
DOI:10.1002/ejoc.200400351

Reference yield:

: 16378-06-6
3-(3-thienyl)propanoic acid

: 827609-27-8
N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 54 percent / phosphorus pentoxide; methanesulfonic acid / 0.67 h / 20 °C

2.1: KOH; iodobenzene diacetate / methanol / 24 h / 20 °C

2.2: 70 percent / HCl / ethanol / 4 h / 20 °C

3.1: 1.35 g / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 8 h / 20 °C

4.1: 80 percent / HCl / methanol / 20 h / 30 °C

5.1: 85 percent / Na₂CO₃; CH₃COOH / methanol / 5 h / pH 4.5 / Heating

6.1: BH₃*THF / tetrahydrofuran / 6 h / Heating

7.1: 77 percent / potassium hydrogen carbonate; IPAC / H₂O / 2.5 h / 80 °C

With hydrogenchloride; dmap; phosphorus pentaoxide; potassium hydroxide; borane-THF; methanesulfonic acid; [bis(acetoxy)iodo]benzene; sodium carbonate; potassium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1002/ejoc.200400351

Reference yield:

: 5650-52-2
4,5-dihydro-6H-cyclopenta[b]thiophen-6-one

: 827609-27-8
N-[(5R,6R)-5-hydroxy-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl]-2-isopropylbenzenecarboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: KOH; iodobenzene diacetate / methanol / 24 h / 20 °C

1.2: 70 percent / HCl / ethanol / 4 h / 20 °C

2.1: 1.35 g / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 8 h / 20 °C

3.1: 80 percent / HCl / methanol / 20 h / 30 °C

4.1: 85 percent / Na₂CO₃; CH₃COOH / methanol / 5 h / pH 4.5 / Heating

5.1: BH₃*THF / tetrahydrofuran / 6 h / Heating

6.1: 77 percent / potassium hydrogen carbonate; IPAC / H₂O / 2.5 h / 80 °C

With hydrogenchloride; dmap; potassium hydroxide; borane-THF; [bis(acetoxy)iodo]benzene; sodium carbonate; potassium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1002/ejoc.200400351