Scopine

Base Information

• Chemical Name: Scopine
• CAS No.: 498-46-4
• Molecular Formula: C8H13NO2
• Molecular Weight: 155.197
• UNII: Z5LGM3Q28U
• DSSTox Substance ID: DTXSID801030466,DTXSID301151677
• Nikkaji Number: J404.695A,J306.683E
• Wikipedia: Scopine
• Wikidata: Q76120007,Q7434451
• ChEMBL ID: CHEMBL4303435,CHEMBL4303536
• Mol file: 498-46-4.mol

Synonyms:Scopine;498-45-3;6,7-Epoxytropine;(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol;Z5LGM3Q28U;498-46-4;(1R,2R,4S,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol;rel-(1R,2R,4S,5S,7s)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol;Pseudoscopine;Scopanol;Scopin;7-Epoxytropine;UNII-Z5LGM3Q28U;SCHEMBL9889341;CHEMBL4303435;CHEMBL4303536;SCHEMBL18577687;DTXSID301151677;DTXSID801030466;HMS3656M14;HMS3884D08;HY-B0459;MFCD06658282;s2545;AKOS015919589;AKOS025400980;AC-3388;CCG-266261;S0912;SW219096-1;AB01566856_01;A871709;Q7434451;1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL, 6.BETA.,7.BETA.-EPOXY-;(1alpha,2beta,4beta,5alpha,7beta)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02.4]nonan-7-ol;(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.)-9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.02,4)NONAN-7-OL;3-Oxa-9-azatricyclo(3.3.1.0(2,4))nonan-7-ol, 9-methyl-, (1alpha,2beta,4beta,5alpha,7beta)-;3-Oxa-9-azatricyclo[3.3.1.02,4]nonan-7-ol, 9-methyl-, (1alpha,2beta,4beta,5alpha,7alpha)-

Chemical Property of Scopine

Chemical Property:

• PSA: 36.00000
• LogP: -0.47100
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(CC1C3C2O3)O
• Isomeric SMILES: CN1[C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)O
• Uses: Isoscopineis a derivative of Scopine (S199975), an intermediate in the production of Tiotropium Bromide, a long-acting bronchodilator.

Technology Process of Scopine

There total 19 articles about Scopine 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: 100.0%

pseudoscopine benzyl ether (132622-34-5,132697-33-7) → pseudoscopine (498-46-4)

Guidance literature:

With methanesulfonic acid; hydrogen; palladium on activated charcoal; In methanol; for 4h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00008a037

Reference yield: 83.0%

pseudoscopine t-butyldimethylsilyl ether (182211-65-0) → pseudoscopine (498-46-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 18h;

DOI:10.1016/0040-4020(96)00693-X

Reference yield:

cyclohepta-3,5-dien-1-ol (1121-63-7) → pseudoscopine (498-46-4)

Guidance literature:

Multi-step reaction with 11 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: 79 percent / dimethylsulfoxide / 3 h / 80 °C

4: 84 percent / 2M NaOH / methanol / 4 h / Heating

5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C

6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight

7: 95 percent / Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

8: Et₃N / tetrahydrofuran / 2 h / Ambient temperature

9: K₂CO₃ / methanol / 120 h

10: 1) naphthalene, Na / 1) DME, -78 deg C, 40 min, 2)a) -78 deg C, 15 min, b) r.t., 40 min

11: 100 percent / MeSO₃H, H₂ / 10percent Pd/C / methanol / 4 h / 760 Torr / Ambient temperature

With 1H-imidazole; sodium hydroxide; naphthalene; methanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium; sodium hydride; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; p-benzoquinone; lithium chloride; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo00008a037

upstream raw materials:

6exo,7exo-epoxy-tropan-3-one

pseudoscopine benzyl ether

pseudoscopine t-butyldimethylsilyl ether

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

Downstream raw materials:

meta-hydroxybenzaldehyde

formaldehyd

methylamine

Refernces

• 1、 Justice, David E.,Malpass, John R.. "Exo- and Endo-6-Hydroxy- and 6,7-Epoxytropanes; Total Synthesis of Scopine, Pseudoscopine, and Nor- Derivatives". . p. 4689 - 4692. Retrieved 2007/10/02.