Sparteine, sulfate

Base Information

• Chemical Name: Sparteine, sulfate
• CAS No.: 299-39-8
• Molecular Formula: C₁₅H₂₆N₂*2H₂O₄S
• Molecular Weight: 430.544
• European Community (EC) Number: 206-078-4
• NSC Number: 376144,402663,143087,26253
• DSSTox Substance ID: DTXSID50952348
• NCI Thesaurus Code: C152415
• ChEMBL ID: CHEMBL1968726
• Mol file: 299-39-8.mol

Synonyms:7,14-Methano-2H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocine, dodecahydro-, (7S-(7alpha,7aalpha,14alpha,14abeta))-;alpha Isosparteine;alpha-Isosparteine;Anhydrous, Sparteine Sulfate;beta Isosparteine;beta-Isosparteine;D-sparteine;Depasan Retard;Genisteine Alkaloid;L-Sparteine;Lupinidin;Lupinidine;Pachycarpine;Pachycarpine Sulfate (1:1), Pentahydrate, (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine;Sparteine Hydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Hydrochloride, (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Hydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Monohydrochloride, (7R-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Monohydroiodide, (7R-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Sulfate;Sparteine Sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14aalpha))-Isomer;Sparteine Sulfate (1:1), (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine Sulfate Anhydrous;Sparteine, (+)-Isomer;Sparteine, (-)-Isomer;Sparteine, (7R-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine, (7R-(7alpha,7abeta,14alpha,14abeta))-Isomer;Sparteine, (7S-(7alpha,7aalpha,14alpha,14aalpha))-Isomer;Sparteine, (7S-(7alpha,7aalpha,14alpha,14abeta))-Isomer;Sparteine, (7S-(7alpha,7abeta,14alpha,14abeta))-Isomer;Sulfate Anhydrous, Sparteine

Chemical Property of Sparteine, sulfate

Chemical Property:

• Vapor Pressure: 2.61E-11mmHg at 25°C
• Melting Point: 135°C
• Boiling Point: 340.9°Cat760mmHg
• Flash Point: 148.3°C
• PSA: 89.46000
• Density: g/cm³
• LogP: 2.64890
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Ethanol (Sparingly, Sonicated), Methanol (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 332.17697855
• Heavy Atom Count: 22
• Complexity: 344

Purity/Quality:

98%,99%, ^*data from raw suppliers

SparteineSulfate ^*data from reagent suppliers

Safty Information:

• Statements: 23/25-33
• Safety Statements: 1-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CC3CC(C2C1)CN4C3CCCC4.OS(=O)(=O)O
• Uses: A class 1a antiarrhythmic agent; a sodium channel blocker.

Technology Process of Sparteine, sulfate

There total 12 articles about Sparteine, sulfate 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: 60.0%

(1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane-8,16-dione (489-54-3,52345-93-4) → (-)-sparteine; bis-hydrogen sulfate (299-39-8,3735-89-5,52670-59-4,98976-05-7)

Guidance literature:

(1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 16h; Reflux; Inert atmosphere;

With sulfuric acid; In water;

DOI:10.1002/anie.201710261

Reference yield:

2-ethoxycarbonylmethylpiperidine (2739-99-3) → (-)-sparteine; bis-hydrogen sulfate (299-39-8,3735-89-5,52670-59-4,98976-05-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2.1: Lipase from Burkholeria cepacia / water; tetrahydrofuran; aq. phosphate buffer / 39 h / 35 °C / pH 7 / Enzymatic reaction

3.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 16 h / 20 °C

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

4.2: 16 h / 20 °C / Inert atmosphere

5.1: ammonium formate; 10 wt% Pd(OH)2 on carbon / ethanol / 4 h / Reflux

5.2: 16 h / Reflux

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux; Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; 10 wt% Pd(OH)2 on carbon; Lipase from Burkholeria cepacia; ammonium formate; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; aq. phosphate buffer; ethanol; hexane; dichloromethane; water; 4.1: |Michael Addition / 4.2: |Michael Addition;

DOI:10.1002/anie.201710261

Reference yield:

ethyl 2-(pyridinyl-2)acetate (2739-98-2) → (-)-sparteine; bis-hydrogen sulfate (299-39-8,3735-89-5,52670-59-4,98976-05-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: platinum(IV) oxide; hydrogenchloride; hydrogen / ethanol; water / 24 h / 20 °C

2.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

3.1: Lipase from Burkholeria cepacia / water; tetrahydrofuran; aq. phosphate buffer / 39 h / 35 °C / pH 7 / Enzymatic reaction

4.1: dicyclohexyl-carbodiimide; dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 16 h / 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

6.2: 16 h / Reflux

7.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.2: 16 h / 20 °C

8.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

8.2: 16 h / 20 °C / Inert atmosphere

9.1: ammonium formate; 10 wt% Pd(OH)2 on carbon / ethanol / 4 h / Reflux

9.2: 16 h / Reflux

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 °C / Reflux; Inert atmosphere

With hydrogenchloride; dmap; platinum(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; 10 wt% Pd(OH)2 on carbon; Lipase from Burkholeria cepacia; hydrogen; ammonium formate; diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; aq. phosphate buffer; ethanol; hexane; dichloromethane; water; acetonitrile; 8.1: |Michael Addition / 8.2: |Michael Addition;

DOI:10.1002/anie.201710261

upstream raw materials:

(1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione

2-ethoxycarbonylmethylpiperidine

ethyl 2-(pyridinyl-2)acetate

tert-butyl 2-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

Downstream raw materials:

(-)-17-oxosparteine

(-)-sparteine

Refernces