4850. Hygrine
Nomenclature
CAS number: 496-49-1
1-[(2R)-1-Methyl-2-pyrrolidinyl]-2-propanone; (+)-N-methyl-2-acetonylpyrrolidine. C8H15NO; mol wt 141.21.
C 68.04%, H 10.71%, N 9.92%, O 11.33%.
Description and references
Occurs in leaves of Erythroxylon coca Lam., Erythroxylaceae of diverse origin: Liebermann, Ber. 22, 677 (1889). Synthesis: Galinovsky et al., Monatsh. Chem. 82, 551 (1951); Lukes et al., Collect. Czech. Chem. Commun. 24, 2433 (1959); Leonard, Cook, J. Am. Chem. Soc. 81, 5627 (1959). Enzymatic synthesis: Tuppy, Faltaous, Monatsh. Chem. 91, 167 (1960). Stereochemistry: Galinovsky et al., ibid. 84, 798 (1953). Absolute configuration: Lukes et al., Collect. Czech. Chem. Commun. 25, 483 (1960).
Properties
Liquid. bp11 76.5°; bp14 81°. nD20 1.4555. Sol in alcohol, chloroform, dil acids; slightly sol in water.Derivative
Oxime.C8H16N2O; mol wt 156.23.
C 61.50%, H 10.32%, N 17.93%, O 10.24%.