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

Base Information

• Chemical Name: 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate
• CAS No.: 1012322-44-9
• Molecular Formula: C₂₀H₂₅NO₆
• Molecular Weight: 375.422
• Mol file: 1012322-44-9.mol

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

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

There total 2 articles about 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-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: 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:

(2S,5R,6S)-6-Allyl-5-hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (865474-08-4) → 1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate (1012322-44-9)

Guidance literature:

Multi-step reaction with 2 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

With N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; chloroform;

DOI:10.3184/174751917X14967701766987

Reference yield: 83.0%

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate (1012322-44-9) + n-propylmagnesium bromide (927-77-5) → 1-benzyl 2-methyl (2S,3S,5R,6S)-6-allyl-5-(methoxymethoxy)-3-propylpiperidine-1,2-dicarboxylate (1012322-46-1)

Guidance literature:

n-propylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 - -35 ℃; for 0.333333h; Inert atmosphere;

1-benzyl 2-methyl (5R,6S)-6-allyl-5-(methoxymethoxy)-5,6-dihydropyridine-1,2(4H)-dicarboxylate; In tetrahydrofuran; at -78 - 0 ℃; for 1.5h; Solvent; stereoselective reaction; Inert atmosphere;

DOI:10.3184/174751917X14967701766987

upstream raw materials:

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

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

Downstream raw materials:

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

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