7921. Pseudotropine

Nomenclature

CAS number: 135-97-7
exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol; 1αH,5αH-tropan-3β-ol; 3β-tropanol; ψ-tropine; 3-pseudotropanol.
C8H15NO; mol wt 141.21.
C 68.04%, H 10.71%, N 9.92%, O 11.33%.

Description and references

Stereoisomeric with tropine. Prepn, structure, separation from tropine, and stereochemical configuration: See Tropine. Stereochemical synthesis: J. J. Tufariello et al., J. Am. Chem. Soc. 101, 2435 (1979).

Chemical structure

Properties

Orthorhombic, bipyramidal crystals from petr ether + benzene. mp 109°; bp 241°; pK (15°): 3.80. pH of 0.05 M soln 11.5. Freely sol in water, alcohol, benzene.

Derivative

Hydrochloride.
C8H15NO.HCl; mol wt 177.67.
C 54.08%, H 9.08%, N 7.88%, O 9.01%, Cl 19.95%.

Properties

Needles from alcohol, dec 282°. Soluble in water, hot alcohol.

Derivative

Tropate.
C8H15NO.C9H8O2; mol wt 289.37.
C 70.56%, H 8.01%, N 4.84%, O 16.59%.

Properties

Cryst from benzene, mp 132°.