(3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate

Base Information

• Chemical Name: (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate
• CAS No.: 1052715-52-2
• Molecular Formula: C₁₉H₂₄N₂O₆
• Molecular Weight: 376.409
• Mol file: 1052715-52-2.mol

Synonyms:(3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate

Chemical Property of (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate

There total 10 articles about (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-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: 75.0%

di-tert-butyl dicarbonate (24424-99-5) + benzyl (3aR,7aS)-2-oxohexahydro[1,3]oxazolo[4,5-c]pyridine-5(4H)-carboxylate (1052715-49-7) → (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate (1052715-52-2)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

3,4-epoxy-piperidine-1-carboxylic acid benzyl ester (66207-08-7,1624258-63-4) → (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate (1052715-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ammonium hydroxide / ethanol; water / 5 h / 70 °C / Sealed tube

1.2: 2 h / 20 °C

2.1: Chiralpak AD-H / n-heptane; ethanol / Resolution of racemate

3.1: triethylamine / dichloromethane / 15 h / 20 °C

4.1: pyridine / 0.17 h / 120 °C / Microwave irradiation

5.1: triethylamine / dmap / dichloromethane / 1 h / 20 °C

With pyridine; ammonium hydroxide; triethylamine; dmap; In ethanol; n-heptane; dichloromethane; water;

Reference yield:

(3R,4R)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)-piperidine-1-carboxylate (1052715-48-6) → (3aR,7aS)-5-benzyl 3-tert-butyl 2-oxotetrahydro-oxazolo[4,5-c]pyridine-3,5(2H,6H)-dicarboxylate (1052715-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0.17 h / 120 °C / Microwave irradiation

2: triethylamine / dmap / dichloromethane / 1 h / 20 °C

With pyridine; triethylamine; dmap; In dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

benzyl (3aR,7aS)-2-oxohexahydro[1,3]oxazolo[4,5-c]pyridine-5(4H)-carboxylate

3,4-epoxy-piperidine-1-carboxylic acid benzyl ester

(trans)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate

Downstream raw materials:

benzyl (3R,4R)-3-(tert-butoxycarbonylamino)-4-(tertbutyldimethylsilyloxy)piperidine-1-carboxylate

5-amino-N-{7-[(3R,4S)-3-amino-4-hydroxypiperidin-1-yl]thieno[3,2-b]pyridin-6-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

C₃₃H₃₄F₂N₆O₇S₂

(3R,5S)-5-amino-N-{4-[3,4-cis-3-amino-4-hydroxypiperidin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide