(6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide

Base Information

• Chemical Name: (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide
• CAS No.: 690656-71-4
• Molecular Formula: C₁₉H₂₃NO₂S
• Molecular Weight: 329.463

Synonyms:(6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide

Chemical Property of (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide

Chemical Property:

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Technology Process of (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide

There total 7 articles about (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-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: 73.0%

L-Phenylalaninol (3182-95-4) + (R)-(+)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid (690656-65-6) → (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide (690656-71-4)

Guidance literature:

(R)-(+)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid; With dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.333333h;

L-Phenylalaninol; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2004.01.036

Reference yield:

4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one (13196-30-0) → (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide (690656-71-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 91 percent / KOH; 18-crown-6 / toluene / 12 h / Heating

2.1: 92 percent / NaBH₄ / methanol / 12 h / 20 °C

3.1: 90 percent / DMAP; pyridine / diethyl ether / 12 h / 20 °C

4.1: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

5.1: 92 percent / NaOH / ethane-1,2-diol / 3 h / 140 - 150 °C

6.1: (R)-(+)-α-phenethylamine / acetone / 1.5 h

6.2: aq. HCl / diethyl ether

7.1: N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.33 h / 0 °C

7.2: 73 percent / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; 18-crown-6 ether; boron trifluoride diethyl etherate; (R)-1-phenyl-ethyl-amine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; ethylene glycol; acetone; toluene;

DOI:10.1016/j.tetasy.2004.01.036

Reference yield:

5,5-dimethyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one (690656-60-1) → (6R)-(+)-N-[(1S)-1-benzyl-2-hydroxyethyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide (690656-71-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / NaBH₄ / methanol / 12 h / 20 °C

2.1: 90 percent / DMAP; pyridine / diethyl ether / 12 h / 20 °C

3.1: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

4.1: 92 percent / NaOH / ethane-1,2-diol / 3 h / 140 - 150 °C

5.1: (R)-(+)-α-phenethylamine / acetone / 1.5 h

5.2: aq. HCl / diethyl ether

6.1: N,N-dicyclohexylcarbodiimide / CH₂Cl₂ / 0.33 h / 0 °C

6.2: 73 percent / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; (R)-1-phenyl-ethyl-amine; dicyclohexyl-carbodiimide; In methanol; diethyl ether; dichloromethane; ethylene glycol; acetone;

DOI:10.1016/j.tetasy.2004.01.036

upstream raw materials:

L-Phenylalaninol

(R)-(+)-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid

4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one

5,5-dimethyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one

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