ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate

Base Information

• Chemical Name: ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate
• CAS No.: 1258422-25-1
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348

Synonyms:ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate

Chemical Property of ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate

Chemical Property:

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Technology Process of ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate

There total 3 articles about ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate 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: 75.0%

ethyl 2-{allyl[(S)-1-phenylethyl]amino}pent-4-enoate (1258422-16-0) → ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate (1258422-25-1) + ethyl (S)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate (1258422-24-0)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; In dichloromethane; at 20 ℃; Reagent/catalyst; Overall yield = 91 %; Overall yield = 165 mg; Inert atmosphere;

DOI:10.1016/j.tetasy.2017.01.001

Reference yield:

(R)-N-[(S)-(1-phenylethyl)amino]pent-4-enoic acid ethyl ester → ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate (1258422-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2017.01.001

Reference yield:

N-[(S)-1-phenylethyl]pent-4-enoic acid → ethyl (R)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate (1258422-25-1) + ethyl (S)-1-[(S)-1-phenylethyl]-1,2,3,6-tetrahydropyridine-2-carboxylate (1258422-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 15 h / 20 °C / Reflux

2: potassium carbonate / N,N-dimethyl-formamide

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) tetraethanolate; thionyl chloride; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2017.01.001

upstream raw materials:

ethyl 2-{allyl[(S)-1-phenylethyl]amino}pent-4-enoate

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