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

Base Information

• Chemical Name: 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate
• CAS No.: 1012322-43-8
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 1012322-43-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate 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: 98.0%

(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (865474-08-4) + chloromethyl methyl ether (107-30-2) → 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate (1012322-43-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1055/s-2007-1000831

Reference yield: 79.0%

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)piperidine-1,2-dicarboxylate (1012322-43-8) → 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate (1012322-44-9)

Guidance literature:

With Phenylselenyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1055/s-2007-1000831

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:

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

chloromethyl methyl ether

Downstream raw materials:

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

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

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

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