methyl (3S,7S,8R,8aS)-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 (3S,7S,8R,8aS)-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.: 755759-19-4
• Molecular Formula: C₂₆H₂₈N₂O₄
• Molecular Weight: 432.519
• Mol file: 755759-19-4.mol

Synonyms:methyl (3S,7S,8R,8aS)-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 (3S,7S,8R,8aS)-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3S,7S,8R,8aS)-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 5 articles about methyl (3S,7S,8R,8aS)-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) + (3S,8R,8aS)-8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine (755759-18-3) → 5-ethyl-1-[(1S)-2-hydroxy-1-phenylethyl]-1H-2-pyridone + methyl (3S,7S,8R,8aS)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-19-4) + methyl (3S,7S,8R,8aS)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (817574-05-3)

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:

(3S,8R,8aS)-8-ethyl-5-oxo-3-phenyl-6-(phenylsulfinyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (817574-42-8) → methyl (3S,7S,8R,8aS)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Na₂CO₃ / toluene / 7 h / Heating

2: LDA; HMPA; CuCN / tetrahydrofuran; cyclohexane / -78 - 20 °C

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

DOI:10.1021/jo0487101

Reference yield:

methyl 4-formylhexanoate (66757-48-0) → methyl (3S,7S,8R,8aS)-8-ethyl-α-(2-indolyl)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-7-acetate (755759-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / Na₂SO₄ / diethyl ether / 1 h / 0 °C

2: 96 percent / KH / tetrahydrofuran / 1.5 h / Heating

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

4: LDA; HMPA; CuCN / tetrahydrofuran; cyclohexane / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydride; sodium carbonate; sodium sulfate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; cyclohexane; toluene;

DOI:10.1021/jo0487101

upstream raw materials:

methyl 1H-indole-2-acetate

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

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

methyl 4-formylhexanoate

Downstream raw materials:

(1R,5S,6S,12R)-12-ethyl-2-[(1S)-2-hydroxy-1-phenylethyl]-6-(methoxycarbonyl)-3-oxo-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole