methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Base Information

Chemical Name:methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate
CAS No.:1379615-12-9
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Synonyms:methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

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Chemical Property of methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

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Technology Process of methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

There total 3 articles about methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate 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: 47.0%

: 1379615-05-0
methyl (1R,2S,3R,10bR)-1-formyl-8,9-dimethoxy-2-(4-methoxyphenyl)-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 1379615-12-9
methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Guidance literature:: (methoxymethyl)triphenylphosphonium chloride; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.333333h; Inert atmosphere;

methyl (1R,2S,3R,10bR)-1-formyl-8,9-dimethoxy-2-(4-methoxyphenyl)-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate; In tetrahydrofuran; toluene; at -78 ℃; for 1h; Inert atmosphere;
DOI:10.1002/chem.201200108

Reference yield:

: 20232-39-7
3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride

: 1379615-12-9
methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium carbonate / dichloromethane / 26 h / 20 °C

1.2: 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.33 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium hexamethyldisilazane; sodium carbonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.201200108

Reference yield:

: 1963-36-6
4-methoxycinnamaldehyde

: 1379615-12-9
methyl (1S,2S,3R,10bR)-8,9-dimethoxy-2-(4-methoxyphenyl)-1-[(E)-2-methoxyvinyl]-3-methyl-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium carbonate / dichloromethane / 26 h / 20 °C

1.2: 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.33 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; sodium hexamethyldisilazane; sodium carbonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.201200108