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

Base Information

• Chemical Name: (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 152555-02-7
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• Mol file: 152555-02-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 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: 85.0%

carbon monoxide (201230-82-2) + N-[(1R)-2-hydroxy-1-phenylethyl]but-3-enamide (1115302-59-4) → (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine (152615-80-0) + (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (152555-02-7)

Guidance literature:

With (acetylacetonato)dicarbonylrhodium (l); hydrogen; toluene-4-sulfonic acid; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); In tetrahydrofuran; at 70 ℃; for 12h; under 3750.38 Torr; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.200801795

Reference yield: 81.0%

2,5-dioxopyrrolidin-1-yl but-3-enoate (388091-45-0) + carbon monoxide (201230-82-2) + D-2-phenylglycinol (56613-80-0) → (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine (152615-80-0) + (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (152555-02-7)

Guidance literature:

With dicarbonylacetylacetonato rhodium(I); hydrogen; pyridinium p-toluenesulfonate; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); In tetrahydrofuran; at 70 ℃; for 12h; under 3750.38 Torr; diastereoselective reaction; Autoclave;

DOI:10.1021/ol902279m

Reference yield: 73.0%

methyl 4-formylbutanoate (6026-86-4) + D-2-phenylglycinol (56613-80-0) → (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine (152615-80-0) + (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (152555-02-7)

Guidance literature:

With 4 Angstroem MS; In toluene; for 36h; Heating;

DOI:10.1021/jo991816p

upstream raw materials:

methyl 4-formylbutanoate

D-2-phenylglycinol

(-)-2-cyano-6-phenyloxazolopiperidine

Acetic acid (R)-2-(2,6-dioxo-piperidin-1-yl)-2-phenyl-ethyl ester

Downstream raw materials:

(3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine

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

(1'R,6S)-(+)-1-(2'-hydroxy-1'-phenyl-ethyl)-6-propyl-piperidin-2-one

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