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

Base Information

• Chemical Name: benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-propylpiperidine-1-carboxylate
• CAS No.: 1012322-56-3
• Molecular Formula: C₂₂H₃₃NO₅
• Molecular Weight: 391.508
• Mol file: 1012322-56-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-propylpiperidine-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: 84.0%

1-benzyl 2-methyl (2S,3S,5R,6S)-6-allyl-5-(methoxymethoxy)-3-propylpiperidine-1,2-dicarboxylate (1012322-46-1) → benzyl (2S,3R,5S,6S)-2-allyl-6-(hydroxymethyl)-3-(methoxymethoxy)-5-propylpiperidine-1-carboxylate (1012322-56-3)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-2007-1000831

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-propylpiperidine-1-carboxylate (1012322-56-3)

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: tetrahydrofuran / 1 h / Inert atmosphere

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

With lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; chloroform; 3.1: |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-propylpiperidine-1-carboxylate (1012322-56-3)

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: tetrahydrofuran / 1 h / Inert atmosphere

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

With lithium triethylborohydride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; 2.1: |Michael Addition;

DOI:10.3184/174751917X14967701766987

upstream raw materials:

1-benzyl 2-methyl (2S,3S,5R,6S)-6-allyl-5-(methoxymethoxy)-3-propylpiperidine-1,2-dicarboxylate

(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