2-((E)-{(S)-(6-Methoxyquinolin-4-yl)[(2S)-8-vinylquinuclidin-2-yl]methylimino}methyl)phenol

The title compound, C27H29N3O2, adopts an E configuration with respect to the C=N bond. The molecular structure is stabilized by intermolecular O—H⋯N interactions between a hydroxy H atom and the N atom on the quinoline ring.

The title compound, C 27 H 29 N 3 O 2 , adopts an E configuration with respect to the C N bond. The molecular structure is stabilized by intermolecular O-HÁ Á ÁN interactions between a hydroxy H atom and the N atom on the quinoline ring.

Comment
In recent years, considerable attention has been focused on the Schiff-base ligands, e.g. as organocatalysts or ligands of metal complexes in asymmetric reactions; as biological active compounds owing to their anti-tumour abilities (Yin et al., 2004). We report here the crystal structure of the title Schiff-base compound (Fig. 1).
The molecule of the compound adopts an E configuration with respect to the C═N bond. The dihedral angle between the quinoline ring and the part of spirane C8C18C24 is 63.06°. The dihedral angle between benzene ring and quinoline ring is 65.20°. And it is 54.46° between benzene ring and the spirane part C8C18C24. All the bond lengths are within normal values (Jones, 1986;Hooft et al., 2008), and are comparable with those in the similar Cinchona alkaloid-derived Schiff base compounds as cited above (Zhu, 2011;Xie et al., 2010). The molecular conformation is stabilized by O-H···N interactions (Table 1).
And then added one more scoop each hour. After four hours, the temperature was slowly cooling down to room temperature.
Then the mixture was filtrated and the residue was washed with Et 2 O. The combined organic layers were removed under reduced pressure. The residue was purified by flash chromatography on silica gel (CH 2 Cl 2 /methanol/Et 3 N 30/1/1) to afford Schiff base compound 1 b (570 mg, 84% yield) as a yellow solid. HRMS (ESI, M+H) calcd for C 27 H 30 N 3 O 2 428.2338, found 428.2333.