methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate

Base Information

• Chemical Name: methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate
• CAS No.: 1357385-46-6
• Molecular Formula: C₂₆H₃₁NO₆
• Molecular Weight: 453.535
• Mol file: 1357385-46-6.mol

Synonyms:methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate

Chemical Property of methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate

There total 9 articles about methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[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:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-46-6) + methyl (2R,3S,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-55-7) + (2R,3R,11bR)-methyl 2-(2-(benzyloxy)ethyl)-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-47-7) + methyl (2R,3S,11bR)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h

2: hydrogenchloride / 1,4-dioxane; dichloromethane / 1.5 h / 20 °C / Cooling with ice

3: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With hydrogenchloride; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 2: Pictet-Spengler cyclisation;

DOI:10.1002/ejoc.201101296

Reference yield:

C17H22O6 → methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-46-6) + methyl (2R,3S,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-55-7) + (2R,3R,11bR)-methyl 2-(2-(benzyloxy)ethyl)-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-47-7) + methyl (2R,3S,11bR)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane; dichloromethane / 1.5 h / 20 °C / Cooling with ice

2: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With hydrogenchloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Pictet-Spengler cyclisation;

DOI:10.1002/ejoc.201101296

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → methyl (2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-46-6) + methyl (2R,3S,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-55-7) + (2R,3R,11bR)-methyl 2-(2-(benzyloxy)ethyl)-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-47-7) + methyl (2R,3S,11bR)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate (1357385-57-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

1.2: 0.75 h / -78 °C / Inert atmosphere

2.1: 17 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 2.33 h / -78 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

4.2: 1.25 h / -78 - 20 °C / Inert atmosphere

5.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / ethanol / 64 h / 20 °C

6.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 1.5 h / 20 °C / Cooling with ice

7.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With hydrogenchloride; oxalyl dichloride; (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; diisobutylaluminium hydride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; cyclohexane; 1.1: Swern oxidation / 1.2: Swern oxidation / 4.1: Swern oxidation / 4.2: Swern oxidation / 6.1: Pictet-Spengler cyclisation;

DOI:10.1002/ejoc.201101296

upstream raw materials:

3-benzyloxypropan-1-ol

3-Benzyloxypropanal

benzyl bromide

5-benzyloxy-2(E)-pentenoic acid methyl ester

Downstream raw materials:

isoemetine

emetine

{(2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl}methanol

(2R,3R,11bS)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-3-vinyl-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline