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

Base Information

• Chemical Name: 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
• CAS No.: 1357385-57-9
• Molecular Formula: C₂₆H₃₁NO₆
• Molecular Weight: 453.535
• Mol file: 1357385-57-9.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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) → (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: 2 h / 40 °C

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

DOI:10.1002/ejoc.201101296

Reference yield:

tert-butyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate (98062-25-0) → (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: 2 h / 40 °C

With hydrogenchloride; In 1,4-dioxane; dichloromethane; 1: Pictet-Spengler cyclisation;

DOI:10.1002/ejoc.201101296

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

upstream raw materials:

3-benzyloxypropan-1-ol

3-Benzyloxypropanal

benzyl bromide

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