(2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide

Base Information

• Chemical Name: (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide
• CAS No.: 280559-72-0
• Molecular Formula: C₂₄H₃₅N₅O₂
• Molecular Weight: 425.574

Synonyms:(2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide

Chemical Property of (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide

There total 6 articles about (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide 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: 92.0%

1-(4-methyl-3-pentenyl)-4-aminopiperidine (185030-43-7) + (2R,5R)-2-tert-butyl-5-[(1S,3S)-3-azidocyclopentyl]-5-phenyl-1,3-dioxolan-4-one (280559-71-9) → (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide (280559-72-0)

Guidance literature:

(2R,5R)-2-tert-butyl-5-[(1S,3S)-3-azidocyclopentyl]-5-phenyl-1,3-dioxolan-4-one; With sodium hydroxide; In methanol; water; at 20 ℃; for 14h;

1-(4-methyl-3-pentenyl)-4-aminopiperidine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 ℃; for 18h;

DOI:10.1016/S0968-0896(00)00008-0

Reference yield:

cyclopent-2-enone (930-30-3) → (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide (280559-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

1.2: 31 percent / tetrahydrofuran / 2 h / -70 °C

2.1: 33 percent / NaBH₄ / methanol / 1 h / -78 - 0 °C

3.1: Et₃N / ethyl acetate / 1 h / 0 °C

4.1: 9.55 g / NaN₃ / dimethylformamide / 1 h / 90 °C

5.1: NaOH / H₂O; methanol / 14 h / 20 °C

5.2: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt / CHCl₃ / 18 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; sodium azide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; cyclohexane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: Reduction / 3.1: Substitution / 4.1: Substitution / 5.1: Hydrolysis / 5.2: Substitution;

DOI:10.1016/S0968-0896(00)00008-0

Reference yield:

(2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one (116907-30-3) → (2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-azidocyclopentyl]-2-hydroxy-2-phenylacetamide (280559-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

1.2: 31 percent / tetrahydrofuran / 2 h / -70 °C

2.1: 33 percent / NaBH₄ / methanol / 1 h / -78 - 0 °C

3.1: Et₃N / ethyl acetate / 1 h / 0 °C

4.1: 9.55 g / NaN₃ / dimethylformamide / 1 h / 90 °C

5.1: NaOH / H₂O; methanol / 14 h / 20 °C

5.2: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt / CHCl₃ / 18 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; sodium azide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; cyclohexane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: Reduction / 3.1: Substitution / 4.1: Substitution / 5.1: Hydrolysis / 5.2: Substitution;

DOI:10.1016/S0968-0896(00)00008-0

upstream raw materials:

1-(4-methyl-3-pentenyl)-4-aminopiperidine

(2R,5R)-2-tert-butyl-5-[(1S,3S)-3-azidocyclopentyl]-5-phenyl-1,3-dioxolan-4-one

cyclopent-2-enone

(2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one

Downstream raw materials:

(2R)-N-[1-(4-methyl-3-pentenyl)piperidin-4-yl]-2-[(1S,3S)-3-aminocyclopentyl]-2-hydroxy-2-phenylacetamide

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