4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 475095-03-5
• Molecular Formula: C₁₈H₂₀N₂O₄
• Molecular Weight: 328.368

Synonyms:4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester

Chemical Property of 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester

There total 3 articles about 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester 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: 95.0%

benzyl 4-oxo-1-piperidinecarboxylate (19099-93-5) + ethyl 2-cyanoacetate (105-56-6) → 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester (475095-03-5)

Guidance literature:

With ammonium acetate; acetic acid; In toluene; for 48h; Inert atmosphere; Dean-Stark; Reflux;

DOI:10.1021/jacs.5b10299

Reference yield:

4-piperidone hydrochloride (41979-39-9) → 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester (475095-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / tetrahydrofuran; water / 0 - 20 °C

2: ammonium acetate; acetic acid / toluene / 48 h / Inert atmosphere; Dean-Stark; Reflux

With ammonium acetate; potassium carbonate; acetic acid; In tetrahydrofuran; water; toluene;

DOI:10.1021/jacs.5b10299

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester (475095-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / tetrahydrofuran; water / 0 - 20 °C

2: ammonium acetate; acetic acid / toluene / 48 h / Inert atmosphere; Dean-Stark; Reflux

With ammonium acetate; potassium carbonate; acetic acid; In tetrahydrofuran; water; toluene;

DOI:10.1021/jacs.5b10299

upstream raw materials:

benzyl 4-oxo-1-piperidinecarboxylate

ethyl 2-cyanoacetate

4-piperidone hydrochloride

benzyl chloroformate

Downstream raw materials:

4-benzyl-4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester

benzyl 4-oxo-3,4-dihydro-1H-spiro[naphthalene-2,4'-piperidine]-1'-carboxylate

3-{1-(4-chloro-benzyl)-2-[4-cyclohexyl-4-(1H-tetrazol-5-ylmethyl)-piperidin-1-yl]-2-oxo-ethylcarbamoyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

{1-(4-chloro-benzyl)-2-[4-cyclohexyl-4-(1H-tetrazol-5-ylmethyl)-piperidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

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