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

Base Information

• Chemical Name: (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 755759-23-0
• Molecular Formula: C₂₇H₃₀N₂O₂S₂
• Molecular Weight: 478.679
• Mol file: 755759-23-0.mol

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

Chemical Property of (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-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,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

There total 6 articles about (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-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: 93.0%

2-(1',3'-Dithian-2'-yl)indole (115127-30-5) + (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (457622-91-2) → (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (755759-23-0)

Guidance literature:

2-(1',3'-Dithian-2'-yl)indole; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; for 2h;

(3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine; In tetrahydrofuran; hexane; at 20 ℃; for 16h; Further stages.;

DOI:10.1016/j.tetlet.2007.07.079

Reference yield: 73.0%

2-(1',3'-Dithian-2'-yl)indole (115127-30-5) + (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (457622-91-2) → (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (755759-23-0) + (3R,7S,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (755759-06-9)

Guidance literature:

2-(1',3'-Dithian-2'-yl)indole; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; for 2h;

(3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine; In tetrahydrofuran; hexane; at -78 ℃; for 12h; Further stages.;

DOI:10.1016/j.tetlet.2007.07.079

Reference yield:

methyl 4-formylhexanoate (66757-48-0) → (3R,7R,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-1,3-dithiolan-2-yl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (755759-23-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Na₂SO₄ / diethyl ether / 0 °C

2: 95 percent / KH / tetrahydrofuran / 1.5 h / Heating

3: 85 percent / Na₂CO₃ / toluene / 7 h / Heating

4: 18 percent / n-BuLi / tetrahydrofuran; cyclohexane / 20 h / 0 °C

With n-butyllithium; potassium hydride; sodium carbonate; sodium sulfate; In tetrahydrofuran; diethyl ether; cyclohexane; toluene;

DOI:10.1021/jo0487101

upstream raw materials:

2-(1',3'-Dithian-2'-yl)indole

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

methyl 4-formylhexanoate

D-2-phenylglycinol

Downstream raw materials:

C₂₄H₂₆N₂O₂

C₂₄H₃₀N₂O