N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

Base Information

Chemical Name:N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide
CAS No.:152004-91-6
Molecular Formula:C₁₃H₁₂ClF₃N₂O
Molecular Weight:304.699
Hs Code.:

Synonyms:N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

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Chemical Property of N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

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Technology Process of N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

There total 9 articles about N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide 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:

: (1S,6S)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enylamine

: 407-25-0
trifluoroacetic anhydride

: 152004-91-6
N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

: N-[(1S,6S)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

Guidance literature:: With triethylamine; In dichloromethane; at 23 ℃; for 0.5h;
DOI:10.1021/jo00073a013

Reference yield:

: 5326-23-8
6-Chloro-3-pyridinecarboxylic acid

: 152004-91-6
N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

Guidance literature:: Multi-step reaction with 9 steps

1: 60 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2: 88 percent / PCC / CH₂Cl₂ / 2 h / 23 °C

3: 89 percent / KHMDS, 18-crown-6*CH₃CN / tetrahydrofuran / 1 h / -78 °C

4: 95 percent / toluene / 24 h / 190 °C

5: 100 percent / LiOH / tetrahydrofuran / 5 h / 23 °C

6: Et₃N, (PhO)2P(=O)N₃ / toluene / 2 h / 85 °C

7: 95 percent / 12 h / 85 °C

8: TBAF / tetrahydrofuran / 4 h / 55 °C

9: Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

With lithium hydroxide; lithium aluminium tetrahydride; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 18-crown-6 complexed with acetonitrile; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo00073a013

Reference yield:

: 23100-12-1
6-chloronicotinylaldehyde

: 152004-91-6
N-[(1R,6R)-6-(6-Chloro-pyridin-3-yl)-cyclohex-3-enyl]-2,2,2-trifluoro-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / KHMDS, 18-crown-6*CH₃CN / tetrahydrofuran / 1 h / -78 °C

2: 95 percent / toluene / 24 h / 190 °C

3: 100 percent / LiOH / tetrahydrofuran / 5 h / 23 °C

4: Et₃N, (PhO)2P(=O)N₃ / toluene / 2 h / 85 °C

5: 95 percent / 12 h / 85 °C

6: TBAF / tetrahydrofuran / 4 h / 55 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

With lithium hydroxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 18-crown-6 complexed with acetonitrile; triethylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo00073a013