(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

Base Information

• Chemical Name: (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
• CAS No.: 817574-08-6
• Molecular Formula: C₂₆H₂₈N₂O₄
• Molecular Weight: 432.519
• Mol file: 817574-08-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 10 articles about (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 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: 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) → (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 (817574-08-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; Heating;

DOI:10.1021/jo0487101

Reference yield: 36.0%

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 (817574-05-3) → (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 (817574-08-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; for 4h; Heating;

DOI:10.1021/jo0487101

Reference yield:

(2S)-2-phenylglycinol (20989-17-7) → (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 (817574-08-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Na₂SO₄ / diethyl ether / 1 h / 0 °C

1.2: 70 °C / 10 - 15 Torr

2.1: KH / tetrahydrofuran / Heating

3.1: Na₂CO₃ / toluene / Heating

4.1: LDA / tetrahydrofuran / -78 °C

4.2: HMPA; CuCN / tetrahydrofuran / 20 °C

5.1: TiCl₄ / CH₂Cl₂ / Heating

With titanium tetrachloride; potassium hydride; sodium carbonate; sodium sulfate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1039/b400987h

upstream raw materials:

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

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

(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