(+)-Galanthamine
Número de catálogo B192826
Peso molecular: 287.35 g/mol
Clave InChI: ASUTZQLVASHGKV-SUYBPPKGSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US06018043
Procedure details
(-)-Narwedine (>98% ee, 0.1 g) was added to a mixture of lithium aluminium hydride (1.2 ml of a 1.0 M solution in ether), (-)-N-methylephedrine (0.23 g) and N-ethyl-2-aminopyridine (0.31 g) in ether at 0° C., and the resulting mixture was stirred at that temperature for 4 h. Sodium hydroxide solution (10 ml of a 1.0 M solution) was added and the product extracted with dichloromethane. Evaporation of the organic phase gave (-)-galanthamine (>98% ee, 85% yield) free of epigalanthamine by GC/MS analysis.
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Yield
85%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C:8]([CH2:10]2)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C@H](N(C)C)[C@H](O)C1C=CC=CC=1.C(N1C=CC=CC1N)C.[OH-].[Na+].CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC>[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:9])[CH2:10]2)[CH2:4][CH2:3]1 |f:1.2.3.4.5.6,9.10|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
|
Step Two
|
Name
|
|
|
Quantity
|
0.1 g
|
|
Type
|
reactant
|
|
Smiles
|
CN1CC[C@@]23C=CC(=O)C[C@@H]2OC4=C(C=CC(=C34)C1)OC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[H-].[Al+3].[Li+].[H-].[H-].[H-]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0.23 g
|
|
Type
|
reactant
|
|
Smiles
|
C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C
|
|
Name
|
|
|
Quantity
|
0.31 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N1C(C=CC=C1)N
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the resulting mixture was stirred at that temperature for 4 h
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the product extracted with dichloromethane
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Evaporation of the organic phase
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 85% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US06018043
Procedure details
(-)-Narwedine (>98% ee, 0.1 g) was added to a mixture of lithium aluminium hydride (1.2 ml of a 1.0 M solution in ether), (-)-N-methylephedrine (0.23 g) and N-ethyl-2-aminopyridine (0.31 g) in ether at 0° C., and the resulting mixture was stirred at that temperature for 4 h. Sodium hydroxide solution (10 ml of a 1.0 M solution) was added and the product extracted with dichloromethane. Evaporation of the organic phase gave (-)-galanthamine (>98% ee, 85% yield) free of epigalanthamine by GC/MS analysis.
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Yield
85%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C:8]([CH2:10]2)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C@H](N(C)C)[C@H](O)C1C=CC=CC=1.C(N1C=CC=CC1N)C.[OH-].[Na+].CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC>[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:9])[CH2:10]2)[CH2:4][CH2:3]1 |f:1.2.3.4.5.6,9.10|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
|
Step Two
|
Name
|
|
|
Quantity
|
0.1 g
|
|
Type
|
reactant
|
|
Smiles
|
CN1CC[C@@]23C=CC(=O)C[C@@H]2OC4=C(C=CC(=C34)C1)OC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[H-].[Al+3].[Li+].[H-].[H-].[H-]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0.23 g
|
|
Type
|
reactant
|
|
Smiles
|
C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C
|
|
Name
|
|
|
Quantity
|
0.31 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N1C(C=CC=C1)N
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the resulting mixture was stirred at that temperature for 4 h
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the product extracted with dichloromethane
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Evaporation of the organic phase
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 85% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US06018043
Procedure details
(-)-Narwedine (>98% ee, 0.1 g) was added to a mixture of lithium aluminium hydride (1.2 ml of a 1.0 M solution in ether), (-)-N-methylephedrine (0.23 g) and N-ethyl-2-aminopyridine (0.31 g) in ether at 0° C., and the resulting mixture was stirred at that temperature for 4 h. Sodium hydroxide solution (10 ml of a 1.0 M solution) was added and the product extracted with dichloromethane. Evaporation of the organic phase gave (-)-galanthamine (>98% ee, 85% yield) free of epigalanthamine by GC/MS analysis.
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Name
Yield
85%
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C:8]([CH2:10]2)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C@H](N(C)C)[C@H](O)C1C=CC=CC=1.C(N1C=CC=CC1N)C.[OH-].[Na+].CN1CC2=C3C(=C(OC)C=C2)OC2C3(C=CC(O)C2)CC1>CCOCC>[CH3:1][N:2]1[CH2:19][C:17]2=[C:18]3[C:13](=[C:14]([O:20][CH3:21])[CH:15]=[CH:16]2)[O:12][C@@H:11]2[C@:5]3([CH:6]=[CH:7][C@H:8]([OH:9])[CH2:10]2)[CH2:4][CH2:3]1 |f:1.2.3.4.5.6,9.10|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
|
Step Two
|
Name
|
|
|
Quantity
|
0.1 g
|
|
Type
|
reactant
|
|
Smiles
|
CN1CC[C@@]23C=CC(=O)C[C@@H]2OC4=C(C=CC(=C34)C1)OC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[H-].[Al+3].[Li+].[H-].[H-].[H-]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
|
Name
|
|
|
Quantity
|
0.23 g
|
|
Type
|
reactant
|
|
Smiles
|
C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C
|
|
Name
|
|
|
Quantity
|
0.31 g
|
|
Type
|
reactant
|
|
Smiles
|
C(C)N1C(C=CC=C1)N
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CCOCC
|
Step Three
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
[Compound]
|
Name
|
solution
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
the resulting mixture was stirred at that temperature for 4 h
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
the product extracted with dichloromethane
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
Evaporation of the organic phase
|
Outcomes
Product
Details
Reaction Time |
4 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| YIELD: PERCENTYIELD | 85% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
