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

Base Information

• Chemical Name: (3R,8aR)-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 817574-16-6
• Molecular Formula: C₁₉H₁₉NO₃S
• Molecular Weight: 341.431
• Mol file: 817574-16-6.mol

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

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

There total 1 articles about (3R,8aR)-5-oxo-3-phenyl-6-(phenylsulfinyl)-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: 97.0%

methyl benzenesulfinate (670-98-4) + (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (152555-02-7) → (3R,8aR)-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (817574-16-6)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1021/jo0487101

Reference yield: 89.0%

(3R,8aR)-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (817574-16-6) → (3R,8aR)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (457622-85-4)

Guidance literature:

With sodium carbonate; In toluene; for 7h; Heating;

DOI:10.1021/jo0487101

Reference yield:

(3R,8aR)-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (817574-16-6) → ((3R,7R,8aR)-5-Oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-7-yl)-acetic acid ethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / Na₂CO₃ / toluene / 7 h / Heating

2: LDA; HMPA / tetrahydrofuran; cyclohexane / 20 h / 0 °C

3: 79 percent / NiCl₂*6H₂O; NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium carbonate; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; cyclohexane; toluene;

DOI:10.1021/jo0487101

upstream raw materials:

methyl benzenesulfinate

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

Downstream raw materials:

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

(3R,7R,8aR)-7-(1,3-dithian-2-yl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

(3R,7R,8aR)-7-[2-(ethoxycarbonyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

methyl (3R,7R,8aR)-α-(1-methyl-2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate