{(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

Base Information

• Chemical Name: {(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
• CAS No.: 1357385-48-8
• Molecular Formula: C₂₅H₃₃NO₄
• Molecular Weight: 411.541
• Mol file: 1357385-48-8.mol

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 11 articles about {(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 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: 49.0%

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) → {(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 (1357385-48-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 16.5h; Reflux;

DOI:10.1002/ejoc.201101296

Reference yield:

methyl (2R)-2-[2-(benzyloxy)ethyl]-9,10-dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline-3-carboxylate → {(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 (1357385-48-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: lithium aluminium tetrahydride / tetrahydrofuran / 16.5 h / 0 °C / Reflux

With lithium aluminium tetrahydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1002/ejoc.201101296

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → {(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 (1357385-48-8)

Guidance literature:

Multi-step reaction with 8 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

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 16.5 h / 0 °C / Reflux

With hydrogenchloride; lithium aluminium tetrahydride; 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:

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

3-benzyloxypropan-1-ol

3-Benzyloxypropanal

benzyl bromide

Downstream raw materials:

isoemetine

emetine

(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

(-)-Protoemetine