Scopine supplier | CasNO.498-45-3

Name
Scopine
EINECS 102-503-4
CAS No. 498-45-3
Article Data11
CAS DataBase
Density 1.284 g/cm3
Solubility
Melting Point 73.0 to 77.0 °C
Formula C₈H₁₃NO₂
Boiling Point 281.3oC at 760 mmHg
Molecular Weight 155.197
Flash Point 123.9oC
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1aH,5aH-Tropan-3a-ol, 6b,7b-epoxy- (8CI);Scopine (6CI,7CI);6,7-Epoxytropine;Scopanol;Scopin;Scopine;
PSA 36.00000
LogP -0.47100

Synthetic route

: 51-34-3, 138-12-5, 64069-63-2, 124917-17-5
scopolamine

: 498-45-3
scopine

Conditions

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 48h;	99.3%
Stage #1: scopolamine With sodium tetrahydroborate In ethanol at 0 - 20℃; for 24h; Stage #2: With hydrogenchloride In diethyl ether; ethanol at 20℃; for 24h;	50%
With ammonium chloride; ammonia at 30℃;

: 114-49-8
hyoscine hydrobromide

: 498-45-3
scopine

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; Cooling with ice;	87%

: 182054-94-0
scopine t-butyldimethylsilyl ether

: 498-45-3
scopine

Conditions

Conditions	Yield
With tert-butyl-ammonium fluoride	82%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 18h;	81%

: 132622-34-5, 132697-33-7
scopine benzyl ether

: 498-45-3
scopine

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; potassium carbonate; palladium on activated charcoal 1) EtOH, 5 atm, r.t, 12h; Yield given. Multistep reaction;

(-)-scopolamine: (-)-scopolamine

: 498-45-3
scopine

Conditions

Conditions	Yield
With NH3-NH4Cl-buffer solution
With bis-1-chloroethyl ether anschliessende Hydrolyse mit wss. Ba(OH)2 und dann mit wss. HCl;

O-acetyl-scopine: O-acetyl-scopine

: 498-45-3
scopine

Conditions

Conditions	Yield
With sodium hydroxide; acetone

: 33250-14-5
Tropilidenoxid

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: LiAlH4 / diethyl ether / 1 h 2: Me4N(1+)IO4(1-) / CH2Cl2 3: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 5: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 6: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 7: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 8: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

Yield

Multi-step reaction with 8 steps
1: LiAlH4 / diethyl ether / 1 h
2: Me4N(1+)IO4(1-) / CH2Cl2
3: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA
4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
5: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
6: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
7: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
8: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

: 1121-63-7
cyclohepta-3,5-dien-1-ol

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: Me4N(1+)IO4(1-) / CH2Cl2 2: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 4: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 5: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 6: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 7: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme
Multi-step reaction with 9 steps 1: NaH / tetrahydrofuran / 15 h / 50 °C 2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h 3: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C 4: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h 5: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 6: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 7: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 8: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 9: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

Yield

Multi-step reaction with 7 steps
1: Me4N(1+)IO4(1-) / CH2Cl2
2: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA
3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
4: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
5: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
6: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
7: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

Multi-step reaction with 9 steps
1: NaH / tetrahydrofuran / 15 h / 50 °C
2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h
3: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C
4: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h
5: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight
6: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature
7: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature
8: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min
9: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h
View Scheme

: 544-25-2
Cyclohepta-1,3,5-triene

norcaradiene-(2.4): norcaradiene-(2.4)

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: aq. CH3COOOH, Na2CO3 / CH2Cl2 / 3 h / 0 °C 2: LiAlH4 / diethyl ether / 1 h 3: Me4N(1+)IO4(1-) / CH2Cl2 4: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 5: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 6: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 7: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 8: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 9: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

Yield

Multi-step reaction with 9 steps
1: aq. CH3COOOH, Na2CO3 / CH2Cl2 / 3 h / 0 °C
2: LiAlH4 / diethyl ether / 1 h
3: Me4N(1+)IO4(1-) / CH2Cl2
4: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA
5: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
6: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
7: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
8: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
9: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

: 1β-hydroxy-4β-<(benzyloxycarbonyl)amino>-6-<(t-butyldimethylsilyl)oxy>cyclohept-2-ene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 68 percent / MCPBA / CH2Cl2 / 3 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 6: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme
Multi-step reaction with 6 steps 1: MCPBA / CH2Cl2 / 3 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 6: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 68 percent / MCPBA / CH2Cl2 / 3 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
6: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

Multi-step reaction with 6 steps
1: MCPBA / CH2Cl2 / 3 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
6: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

: 182054-91-7
N-benzyloxycarbonyl-3α-<(t-butyldimethylsilyl)oxy>-6β,7β-epoxy-8-azabicyclo<3.2.1>octane

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 2: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

: 1β-hydroxy-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 2: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 3: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 4: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 5: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

: 1α-chloro-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 2: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 3: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

: 1β-<(p-toluenesulphonyl)oxy>-2β,3β-epoxy-4β-<(benzyloxycarbonyl)amino>-6α-<(t-butyldimethylsilyl)oxy>cycloheptane

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 2: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 3: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

: N-benzyloxycarbonyl-3α-hydroxy-6-aza-7-oxabicyclo[3.2.2]non-8-ene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h 3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C 4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C 5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating 6: 81 percent / TBAF / tetrahydrofuran / 18 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 1.) Me4N(1+)*IO4(1-), 2.) Imidazole, 3.) Na(Hg), Na3PO4, 4.) MCPBA
2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, RT, 1.5 h
3: 64 percent / LiCl / dimethylsulfoxide / 1.5 h / 55 °C
4: 82 percent / NaH / tetrahydrofuran; 1,2-dimethoxy-ethane / 3 h / 20 - 50 °C
5: 95 percent / LiAlH4 / diethyl ether / 2 h / Heating
6: 81 percent / TBAF / tetrahydrofuran / 18 h
View Scheme

: 115522-58-2
6-(benzyloxy)-1,3-cycloheptadiene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h 2: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C 3: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h 4: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 5: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 6: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 7: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 8: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

Yield

Multi-step reaction with 8 steps
1: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h
2: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C
3: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h
4: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight
5: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature
6: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature
7: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min
8: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h
View Scheme

: 132622-29-8
1β-hydroxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h 2: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 3: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 4: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 5: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 6: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

Yield

Multi-step reaction with 6 steps
1: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h
2: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight
3: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature
4: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature
5: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min
6: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h
View Scheme

: 115522-57-1, 150338-86-6
1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C 2: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h 3: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 4: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 5: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 6: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 7: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

Yield

Multi-step reaction with 7 steps
1: 96 percent / DIBAL / tetrahydrofuran; hexane / 0.75 h / 2 °C
2: 66 percent / Pd(PPh3)4 / acetonitrile / 4 h
3: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight
4: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature
5: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature
6: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min
7: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h
View Scheme

: 132622-31-2, 132697-30-4
1β-(p-toluenesulfonamido)-4-chloro-6α-(benzyloxy)-2-cycloheptene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 2: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 3: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 4: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

: 132622-32-3
1β-(p-toluenesulfonamido)-2β,3β-epoxy-4α-chloro-6α-(benzyloxy)-2-cycloheptene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 2: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 3: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

: 132622-30-1, 132697-31-5
1β-(p-toluenesulfonamido)-4β-hydroxy-6α-(benzyloxy)-2-cycloheptene

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight 2: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature 3: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature 4: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 5: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

Yield

Multi-step reaction with 5 steps
1: 76 percent / LiCl, MsCl, 2,4,6-trimethylpyridine / dimethylformamide / 0 deg C to r.t., overnight
2: 86 percent / m-CPBA / CH2Cl2 / 48 h / Ambient temperature
3: 95 percent / K2CO3 / methanol / 56 h / Ambient temperature
4: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min
5: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h
View Scheme

: 132622-33-4, 132697-32-6
3α-(benzyloxy)-6β,7β-epoxy-8-(p-toluenesulfonyl)-1β-azabicyclo<3.2.1>octane

: 498-45-3
scopine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) naphthalene, Na / 1) THF, -78 deg C, 30 min 2: 1) aq.2M HCl, H2, 2) 10percent aq. K2CO3 / 1) 10percent Pd/C / 1) EtOH, 5 atm, r.t, 12h View Scheme

: 149-64-4
hyoscine-N-butyl bromide

: 498-45-3
scopine

Conditions

Conditions	Yield
With ruthenium trichloride; potassium metaperiodate; diperiodatocuprate(III) dihydrate; water; potassium nitrate; potassium hydroxide at 28℃; for 6h; Kinetics; Catalytic behavior; Concentration; Temperature; Inert atmosphere;

: 498-45-3
scopine

: 74-88-4
methyl iodide

: 21662-36-2
(1R,2R,4S,5S,7S)-7-hydroxy-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-iumiodide (N-methylscopinium)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 48h; Inert atmosphere;	85%

: 4408-82-6
2,2-di(thiophen-2-yl)acetic acid

: 498-45-3
scopine

: 1336913-21-3
C18H19NO3S2

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Product distribution / selectivity;	83%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Reagent/catalyst; Solvent; Concentration;	83%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Product distribution / selectivity;

: 498-45-3
scopine

: 305-03-3
chlorambucil

: C22H30Cl2N2O3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	82.3%

: 26447-85-8
hydroxy-di-thiophen-2-yl-acetic acid methyl ester

: 498-45-3
scopine

: 136310-64-0
N-demethyltiotropium

Conditions

Conditions	Yield
With potassium tert-butylate; 1-butyl-3-methylimidazolium Tetrafluoroborate In tetrahydrofuran at 20℃; for 18h; Solvent; Concentration; Reagent/catalyst; Temperature; Time; Molecular sieve;	73%
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine at 70℃; under 210 Torr; for 1h; Stage #2: With sodium hydride at 70℃; under 210 Torr; for 3h;	42%
With sodium hydride In toluene; mineral oil at 90℃; for 2h;	33%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 70℃; under 15.0015 Torr; for 19h;

: 65-85-0
benzoic acid

: 498-45-3
scopine

: (1R,2R,4S,5S,7r)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl benzoate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -35 - 20℃;	67.9%

: 26447-85-8
hydroxy-di-thiophen-2-yl-acetic acid methyl ester

: 498-45-3
scopine

A: 136310-64-0
N-demethyltiotropium

B: scopoline

C: di-(2-thienyl)glycolic acid scopoline ester

Conditions

Conditions	Yield
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine With sodium t-butanolate In tetrahydrofuran; toluene at 70 - 90℃; under 375.038 Torr; for 4.41667h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water Cooling with ice; Stage #3: With sodium carbonate In water Reagent/catalyst; Solvent; Time; Temperature; Pressure; Concentration; Overall yield = 37.2 g;	A 58% B 5.3 %Chromat. C 6.1 %Chromat.
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine With potassium tert-butylate In toluene at 70 - 90℃; under 225.023 - 300.03 Torr; for 4.25h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water Cooling with ice; Stage #3: With sodium carbonate In water Reagent/catalyst; Temperature; Time; Overall yield = 0.82 g;	A 41% B 18.4 %Chromat. C 5.6 %Chromat.
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine With sodium hydride In toluene; mineral oil at 70 - 90℃; under 225.023 - 300.03 Torr; for 4.25h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene; mineral oil Cooling with ice; Stage #3: With sodium carbonate In water Overall yield = 1.01 g;	A 21% B 35.7 %Chromat. C 30.4 %Chromat.

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: 40997-78-2
2,2-diphenylpropionyl chloride

: 498-45-3
scopine

: scopine 2,2-diphenylpropionate

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 24h;	47%

: 26447-85-8
hydroxy-di-thiophen-2-yl-acetic acid methyl ester

: 498-45-3
scopine

A: 136310-64-0
N-demethyltiotropium

B: scopoline

Conditions

Conditions	Yield
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine With sodium t-butanolate In toluene at 70 - 90℃; under 225.023 - 300.03 Torr; for 4.25h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water Cooling with ice; Stage #3: With sodium carbonate In water Time; Concentration;	A 33% B 26.3 %Chromat.
Stage #1: hydroxy-di-thiophen-2-yl-acetic acid methyl ester; scopine With sodium methylate In toluene at 70 - 90℃; under 75.0075 - 225.023 Torr; for 5.25h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene Cooling with ice; Stage #3: With sodium carbonate In water	A 11.6 %Chromat. B 57.3 %Chromat.

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: 32315-10-9
bis(trichloromethyl) carbonate

: 1717-22-2
2-amino-5-fluorobiphenyl

: 498-45-3
scopine

: (1R,2R,4S,5S,7s,9r)-7-(((5-fluorobiphenyl-2-yl)carbamoyl)oxy)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium chloride

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; scopine In acetonitrile at 0 - 20℃; for 36h; Stage #2: 2-amino-5-fluorobiphenyl With pyridine at 60℃; for 24h;	8%

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: 1140-33-6
1-chloro-4-(diazo(phenyl)methyl)benzene

: 498-45-3
scopine

: 116603-25-9
7t-(4-chloro-benzhydryloxy)-9-methyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.02,4]nonane

Conditions

Conditions	Yield
In benzene at 95 - 100℃; for 5.5h;

: 908093-98-1
diazodiphenylmethane

: 498-45-3
scopine

: 112018-04-9
7t-benzhydryloxy-9-methyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.02,4]nonane

Conditions

Conditions	Yield
In benzene at 80 - 85℃; for 3h;

: 14510-37-3
3-acetoxy-2-phenyl-propionyl chloride

: 98-95-3
nitrobenzene

: 498-45-3
scopine

(+-)-O-acetyl-scopolamine hydrochloride: (+-)-O-acetyl-scopolamine hydrochloride

...Expand

: 110-86-1
pyridine

: 498-45-3
scopine

CrO3: CrO3

A: 498-47-5
6exo,7exo-epoxy-tropan-3-one

B (+-)-N-formyl-norscopolin: (+-)-N-formyl-norscopolin

...Expand

: 498-45-3
scopine

dl-scopolin: dl-scopolin

Conditions

Conditions	Yield
bei der Destillation;

: 498-45-3
scopine

Cr2O3-H2SO4: Cr2O3-H2SO4

dl-scopolin: dl-scopolin

Conditions

Conditions	Yield
at 50 - 60℃;

: 498-45-3
scopine

n KOH-solution: n KOH-solution

dl-scopolin: dl-scopolin

Conditions

Conditions	Yield
at 20℃;

: 14510-37-3
3-acetoxy-2-phenyl-propionyl chloride

: 98-95-3
nitrobenzene

: 498-45-3
scopine

O-<3-acetoxy-2-phenyl-propionyl>-scopolamine hydrochloride: O-<3-acetoxy-2-phenyl-propionyl>-scopolamine hydrochloride

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: 14510-37-3
3-acetoxy-2-phenyl-propionyl chloride

: 498-45-3
scopine

A O-acetyl-scopine hydrochloride: O-acetyl-scopine hydrochloride

B O-<3-acetoxy-2-phenyl>-propionyl>-scopolamine hydrochloride: O-<3-acetoxy-2-phenyl>-propionyl>-scopolamine hydrochloride

...Expand

: 498-45-3
scopine

salts of scopolin: salts of scopolin

: 7790-94-5
chlorosulfonic acid

: 498-45-3
scopine

A scopinesulfuric acid: scopinesulfuric acid

B dl-scopolinsulfuric acid: dl-scopolinsulfuric acid

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Scopine Specification

Scopine, with the CAS NO.498-45-3, is a tropane alkaloid found in a variety of plants including Mandragora root, Senecio mikanoides (Delairea odorata), Scopolia carniolica, and Scopolia lurida. It is also called 1α,2β,4β,5α)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7β-ol;(1β,2α,4α,5β,7α)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol. Scopine can be prepared by the hydrolysis of scopolamine.

Physical properties about Scopine are: (1)ACD/LogP: -0.295; (2)ACD/LogD (pH 5.5): -3.23; (3)ACD/LogD (pH 7.4): -1.82; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Molar Refractivity: 39.857 cm³; (12)Molar Volume: 120.794 cm³; (13)Polarizability: 15.801 10-24cm³; (14)Surface Tension: 46.4469985961914 dyne/cm; (15)Density: 1.285 g/cm³; (16)Flash Point: 123.928 °C; (17)Enthalpy of Vaporization: 60.366 kJ/mol; (18)Boiling Point: 281.303 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H13NO2/c1-9-5-2-4(10)3-6(9)8-7(5)11-8/h4-8,10H,2-3H2,1H3/t4-,5-,6+,7-,8+;
(2)InChIKey=FIMXSEMBHGTNKT-RZVDLVGDSA-N;
(3)SmilesO1[C@H]2[C@H]1[C@H]1C[C@H](C[C@@H]2N1C)O;

Product Name

Scopine

Synthetic route

Scopine Specification

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