beta-Isosparteine

Title: b-Isosparteine
CAS Registry Number: 24915-04-6
CAS Name: [7S-(7a,7ab,14a,14ab)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1¢,2¢-e][1,5]diazocine
Additional Names: pusilline
Molecular Formula: C15H26N2
Molecular Weight: 234.38
Percent Composition: C 76.87%, H 11.18%, N 11.95%
Literature References: Isoln from Lupinus pusillus, Pursh., Leguminosae: Marion, Fenton, J. Org. Chem. 13, 780 (1948). Identity with pusilline: Greenhalgh, Marion, Can. J. Chem. 34, 456 (1956); identity of monohydrochloride with nonalupine and spathulatine: Marion, ibid. 29, 959 (1951). Synthesis: Bohlmann, Ber. 90, 653 (1957). Absolute configuration: Okuda, Tsuda, Chem. Ind. (London) 1961, 1115.
Properties: Oil, bp0.2 100-110°. [a]D32 -15.3° (c = 2.3 in abs alc). Sol in methanol, ethanol. Practically insol in water.
Boiling point: bp0.2 100-110°
Optical Rotation: [a]D32 -15.3° (c = 2.3 in abs alc)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C15H26N2.HCl.H2O
Molecular Weight: 288.86
Percent Composition: C 62.37%, H 10.12%, N 9.70%, Cl 12.27%, O 5.54%
Properties: Prismatic needles from alcohol or acetone. Melts at 88-90°, resolidifies, and remelts at 235.5-236.5°. [a]D -1.88° (c = 5.90 in chloroform); -2.32° (c = 6.42 in alc); -2.44° (c = 6.42 in water). Sol in water, benzene, alcohol, chloroform, carbon tetrachloride, acetone, ethyl acetate; slightly sol in petr ether, ether. The aq soln is slightly alkaline to litmus.
Optical Rotation: [a]D -1.88° (c = 5.90 in chloroform); -2.32° (c = 6.42 in alc); -2.44° (c = 6.42 in water)
Derivative Type: Dihydrochloride
Molecular Formula: C15H26N2.2HCl
Molecular Weight: 307.30
Percent Composition: C 58.63%, H 9.18%, N 9.12%, Cl 23.07%
Properties: Clusters of fine needles from ethyl acetate, mp 270-273° (sinters at 262°).
Melting point: mp 270-273° (sinters at 262°)
Derivative Type: Hydriodide
Molecular Formula: C15H26N2.HI
Molecular Weight: 362.29
Percent Composition: C 49.73%, H 7.51%, N 7.73%, I 35.03%
Properties: Prismatic needles from acetone, mp 252.5° (sinters at 250.5°).
Melting point: mp 252.5° (sinters at 250.5°)
Derivative Type: Methiodide
Molecular Formula: C15H26N2.CH3I
Molecular Weight: 376.32
Percent Composition: C 51.07%, H 7.77%, N 7.44%, I 33.72%
Properties: Diamond-shaped crystals from ethyl acetate, mp 250-252°.
Melting point: mp 250-252°
Status: This monograph has been retired and is no longer subject to revision or update.
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