benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate
• CAS No.: 1012322-55-2
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454

Synonyms:benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate

Chemical Property of benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate

Chemical Property:

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Technology Process of benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate

There total 3 articles about benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-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:

(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (865474-08-4) → benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate (1012322-55-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine / chloroform / 15 h / 0 - 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 1 h / -78 - 0 °C / Inert atmosphere

3.1: copper(l) iodide / diethyl ether / 0.33 h / -78 - -35 °C / Inert atmosphere

3.2: 1 h / -78 - 0 °C / Inert atmosphere

4.1: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With copper(l) iodide; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; chloroform; 3.1: |Michael Addition / 3.2: |Michael Addition;

DOI:10.3184/174751917X14967701766987

Reference yield:

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate (1012322-43-8) → benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate (1012322-55-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C / Inert atmosphere

2.1: copper(l) iodide / diethyl ether / 0.33 h / -78 - -35 °C / Inert atmosphere

2.2: 1 h / -78 - 0 °C / Inert atmosphere

3.1: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With copper(l) iodide; lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; 2.1: |Michael Addition / 2.2: |Michael Addition;

DOI:10.3184/174751917X14967701766987

Reference yield:

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate (1012322-44-9) → benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-methylpiperidine-1-carboxylate (1012322-55-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(l) iodide / diethyl ether / 0.33 h / -78 - -35 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C / Inert atmosphere

2.1: lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With copper(l) iodide; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; 1.1: |Michael Addition / 1.2: |Michael Addition;

DOI:10.3184/174751917X14967701766987

upstream raw materials:

(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate

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