N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Base Information

• Chemical Name: N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide
• CAS No.: 1228029-94-4
• Molecular Formula: C₂₆H₃₈F₃N₃O₃
• Molecular Weight: 497.601

Synonyms:N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Chemical Property of N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Chemical Property:

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Useful:

Technology Process of N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

There total 6 articles about N₂-(tert-butyloxycarbonyl)-N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide 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:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + (3aS,4R,6aR)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine (1228029-90-0) → N2-(tert-butyloxycarbonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide (1228029-94-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 24h;

Reference yield:

C19H25F3N2OS (1449789-69-8) → N2-(tert-butyloxycarbonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide (1228029-94-4)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C

2: sodium tetrahydroborate / methanol / 16 h / -78 - 20 °C

3: triethylamine / dichloromethane / 0.5 h / 25 °C

4: sodium azide / N,N-dimethyl acetamide / 16 h / 90 °C

5: triphenylphosphine; water / tetrahydrofuran / 1 h / 80 °C

6: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; sodium azide; water; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; 5: |Staudinger Azide Reduction;

DOI:10.1016/j.bmcl.2013.06.074

Reference yield:

C15H16F3NO (1449789-70-1) → N2-(tert-butyloxycarbonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide (1228029-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / methanol / 16 h / -78 - 20 °C

2: triethylamine / dichloromethane / 0.5 h / 25 °C

3: sodium azide / N,N-dimethyl acetamide / 16 h / 90 °C

4: triphenylphosphine; water / tetrahydrofuran / 1 h / 80 °C

5: 1,2-dichloro-ethane; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C

With sodium tetrahydroborate; sodium azide; water; benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; 4: |Staudinger Azide Reduction;

DOI:10.1016/j.bmcl.2013.06.074

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

(3aS,4R,6aR)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine

C₁₉H₂₅F₃N₂OS

C₁₅H₁₆F₃NO

Downstream raw materials:

N₁-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

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