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

Base Information

Chemical Name:(3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
CAS No.:1273048-00-2
Molecular Formula:C₃₃H₃₂N₂O₅
Molecular Weight:536.627
Hs Code.:

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

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

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

There total 1 articles about (3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-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: 69.0%

: 4264-35-1
2-acetylindole

: 331473-26-8
8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-6-carboxylic acid benzyl ester

: 1273048-00-2
(3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1273047-23-6
(3R,6S,7S,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:: 8-ethyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine-6-carboxylic acid benzyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

2-acetylindole; In tetrahydrofuran; at -78 - 20 ℃; for 5h; optical yield given as %de;
DOI:10.1002/ejoc.201001020

Reference yield: 65.0%

: 1273048-00-2
(3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1273047-91-8
(3R,7S,8S,8aR)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:: (3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine; With hydrogen; palladium(II) hydroxide; In ethyl acetate; at 20 ℃; for 24h;

In toluene; for 16h; Reflux;
DOI:10.1002/ejoc.201001020

Reference yield:

: 1273048-00-2
(3R,6R,7R,8S,8aR)-6-(benzyloxycarbonyl)-8-ethyl-7-[2-(2-indolyl)-2-oxoethyl]-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogen; palladium(II) hydroxide / ethyl acetate / 24 h / 20 °C

1.2: 16 h / Reflux

2.1: sodium tetrahydroborate / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: pyridine; dmap / dichloromethane / 14 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; hydrogen; palladium(II) hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.201001020