ChemicalBook > CAS DataBase List > [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate

[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate

Product Name
[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate
CAS No.
490-96-0
Chemical Name
[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate
Synonyms
Solanesine;Valeroidine;[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate;Butanoic acid,3-methyl-, (1S,3R,5S,6R)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
CBNumber
CB11254487
Molecular Formula
C13H23NO3
Formula Weight
241.33
MOL File
490-96-0.mol
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[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate Property

Melting point:
85°C
Boiling point:
163-167 °C(Press: 2 Torr)
Density 
1.11±0.1 g/cm3(Predicted)
pka
14.33±0.40(Predicted)
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Hazard and Precautionary Statements (GHS)

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[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate Chemical Properties,Usage,Production

Description

An alkaloid found in Duboisia myoporoides, the base crystallizes from EtOH in colourless, nacreous plates and has [α]20D - 9.0° (c 5.0, EtOH), or - 4.0° (c 5.0, H2O). It yields a crystalline hydrobromide as colourless needles, m.p. l70-2°C; [α]20D + 5.0° (c 20.0, H20); picrate, m.p. lS2-3°C; methiodide, m.p. 20S.SoC and the acetyl derivative, characterized as the hydrobromide, m.p. 197°C. The isovaleryl ester forms a hydrochloride, m.p. l24-SoC; [α]D + 2.6° (c 3.78, EtOH) and a hydrobromide, m.p. l76-7°C. Treatment of the hydrobromide with thionyl chloride gives norvaleroidine due to demethylation, a colourless syrup which furnishes a crystalline hydrobromide, m.p. 270°C; [α]20D + 1 ° (c 20.0, H20). On hydrolysis with aqueous Ba(OHh, the base gives dihydroxytropane and isovaleric acid while oxidation with KMn04 furnishes norvalieroidine and a base C13H190 4N, m.p. 136°C; [α]20D - 16.6° (c 7.4, EtOH).

Definition

ChEBI: Valeroidine is a tropane alkaloid.

References

Barger, Martin, Mitchell.,!. Chem. Soc., 1820 (1937)
Barger, Martin, Mitchell., ibid, 1685 (1938)
Martin, Mitchell., ibid, 1155 (I 940)
Mitchell, Troutner., ibid, 1330 (I 947)
Fodor, Kovacs., ibid, 2341 (1953)
Fodor, Vincze, Toth., ibid, 1349 (1957)
Fodor, Vincze, Toth., ibid, 3219 (1961)

[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate Preparation Products And Raw materials

Raw materials

Preparation Products

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[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate Suppliers

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490-96-0, [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oateRelated Search:

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  • [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate
  • Valeroidine
  • Solanesine
  • Butanoic acid,3-methyl-, (1S,3R,5S,6R)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
  • 490-96-0