tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate

Base Information

• Chemical Name: tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate
• CAS No.: 601489-05-8
• Molecular Formula: C₂₁H₂₉NO₄
• Molecular Weight: 359.466
• Mol file: 601489-05-8.mol

Synonyms:tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate

Chemical Property of tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate

There total 2 articles about tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate 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: 60.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (3R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (194149-77-4) → tert-butyl (3R,6S,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate + tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate (601489-05-8)

Guidance literature:

(3R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine; With lithium hexamethyldisilazane; at -78 ℃; for 1h;

bromoacetic acid tert-butyl ester; at -78 ℃; for 2h;

DOI:10.1021/ol035199+

Reference yield:

(3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (194149-76-3) → tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate (601489-05-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / HCl / methanol / 25 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 2 h

With hydrogenchloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol;

DOI:10.1021/jo060157v

Reference yield: 57.0%

tert-butyl (3R,6R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetate (601489-05-8) → tert-butyl (3R,5R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]piperidine-3-acetate (601489-07-0)

Guidance literature:

With borane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol035199+

upstream raw materials:

bromoacetic acid tert-butyl ester

(3R,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

(3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Downstream raw materials:

tert-butyl (3R,5R)-5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]piperidine-3-acetate

tert-butyl (3R,5R)-1-(tert-butoxycarbonyl)-5-ethylpiperidine-3-acetate