(3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate

Base Information

• Chemical Name: (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate
• CAS No.: 495380-50-2
• Molecular Formula: C₂₈H₃₄N₂O₃
• Molecular Weight: 446.59

Synonyms:(3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate

Chemical Property of (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate

Chemical Property:

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Technology Process of (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate

There total 2 articles about (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate 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: 83.0%

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine (14429-03-9,120343-46-6,140408-66-8) + (E)-tert-butyl-3-(3-pyridyl)prop-2-enoate (181517-74-8) → (3R,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate + (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate (495380-50-2)

Guidance literature:

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(E)-tert-butyl-3-(3-pyridyl)prop-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1039/b204653a

Reference yield:

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) → (3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate (495380-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / CH₂Cl₂ / 16 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 83 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; 1.1: Wittig reaction;

DOI:10.1039/b204653a

Reference yield: 80.0%

(3S,αR)-tert-butyl 3-(N-benzyl-N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate (495380-50-2) → (3S,αR)-tert-butyl 3-(N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate (495380-65-9)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1039/b204653a

upstream raw materials:

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine

(E)-tert-butyl-3-(3-pyridyl)prop-2-enoate

(tert-Butoxycarbonylmethylene)triphenylphosphorane

Downstream raw materials:

(3S,αR)-tert-butyl 3-(N-α-methyl-4-methoxybenzylamino)-3-(3-pyridyl)propanoate

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