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

Base Information

• Chemical Name: methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate
• CAS No.: 755759-16-1
• Molecular Formula: C₂₆H₂₈N₂O₄
• Molecular Weight: 432.519

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

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

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

There total 2 articles about methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-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:

methyl 1H-indole-2-acetate (21422-40-2) + (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (457622-91-2) → methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-22-9) + methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-16-1)

Guidance literature:

methyl 1H-indole-2-acetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b400987h

Reference yield:

methyl 1H-indole-2-acetate (21422-40-2) + (3R,8S,8aR)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (457622-91-2) → 5-ethyl-1-[(1R)-2-hydroxy-1-phenylethyl]-1H-2-pyridone + methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-22-9) + methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-16-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃;

DOI:10.1021/jo0487101

Reference yield: 51.0%

methyl (3R,7R,8S,8aR)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-16-1) → (1S,5R,6R,12S)-12-ethyl-2-[(1R)-2-hydroxy-1-phenylethyl]-6-(methoxycarbonyl)-3-oxo-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole

Guidance literature:

With titanium tetrachloride; In dichloromethane; Heating;

DOI:10.1021/jo0487101

upstream raw materials:

methyl 1H-indole-2-acetate

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

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