(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

Base Information

Chemical Name:(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate
CAS No.:1448530-99-1
Molecular Formula:C₃₃H₃₈N₂O₈
Molecular Weight:590.673
Hs Code.:

(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

Synonyms:(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

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Chemical Property of (5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

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Technology Process of (5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

There total 6 articles about (5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate 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: 41.0%

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 1448530-96-8
(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

: 1448530-98-0
(5S,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

: 1448530-99-1
(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

Guidance literature:: (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trifluoroacetic acid; In chloroform; for 4h;

tert-Butyl acrylate; With triethylamine; In chloroform; at 0 - 20 ℃; Overall yield = 59 %; Overall yield = 985 mg;
DOI:10.1016/j.tet.2013.05.009

Reference yield:

: 1448530-90-2
(1S,3S)-ethyl 8-acetoxy-3-(((tert-butyldimethylsilyl)oxy)-methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

: 1448530-98-0
(5S,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

: 1448530-99-1
(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 60 h / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.75 h / -78 - 0 °C / Inert atmosphere

4.1: trifluoroacetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / chloroform / 4 h

4.2: 0 - 20 °C

With oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform;
DOI:10.1016/j.tet.2013.05.009

Reference yield:

: 1448530-92-4
(1S,3S)-ethyl 8-acetoxy-2-(2-(benzyl(tert-butoxycarbonyl)-amino)acetyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

: 1448530-98-0
(5S,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

: 1448530-99-1
(5R,8S,10R,11R)-10-tert-butyl 5-ethyl 4-acetoxy-13-benzyl-3-methoxy-2-methyl-7-oxo-5,7,8,9,10,11-hexahydro-8,11-epiminoazepinol[1,2-b]isoquinoline-5,10-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.75 h / -78 - 0 °C / Inert atmosphere

3.1: trifluoroacetic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / chloroform / 4 h

3.2: 0 - 20 °C

With oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform;
DOI:10.1016/j.tet.2013.05.009