(3S,4R,4aS,7aR,12bS)-3-Cyclopropylmethyl-4a,9-dihydroxy-3-methyl-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoroacetate methanol solvate

Xu Cai,Song Li,Xinbo Zhou,Wu Zhong,Zhibing Zheng

doi:10.1107/s1600536810041164

Abstract

In the title compound, C21H26F3NO6 +·CF3COO−·CH3OH or S-MNTX·CF3COO−·CH3OH (MNTX = methylnaltrexone), the conformation of the polycyclic backbone of the noroxymorphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings. The dihedral angle between the cyclohexene and piperidine rings is 84.5 (6)°, while the dihedral angles between the planes of cyclohexane ring and the benzene, cyclohexene and piperidine rings, respectively, are 85.8 (6),80.0 (7) and 10.3 (7)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds. The trifluoroacetate F atoms are disordered in a 0.710 (14):0.710 (14) ratio. The absolute stereochemistry was inferred from the use of (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one as one of the starting materials.

Highlights

S-MNTXCF3COOCH3OH (MNTX = methylnaltrexone), the conformation of the polycyclic backbone of the noroxymorphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings
84.5 (6), while the dihedral angles between the planes of cyclohexane ring and the benzene, cyclohexene and piperidine rings, respectively, are 85.8 (6),80.0 (7) and 10.3 (7)
In the crystal structure of the title compound (Fig.1), C24H30F3NO7, the conformation of the polycyclic backbone of the noroxymorphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings

Summary

Mo K radiation

S-MNTXCF3COOCH3OH (MNTX = methylnaltrexone), the conformation of the polycyclic backbone of the noroxymorphone skeleton can be simplified in terms of the angles between the least-squares planes of these rings. The dihedral angle between the cyclohexene and piperidine rings is. 84.5 (6) , while the dihedral angles between the planes of cyclohexane ring and the benzene, cyclohexene and piperidine rings, respectively, are 85.8 (6),80.0 (7) and 10.3 (7). Molecules are linked by O—H O hydrogen bonds

The trifluoroacetate F atoms are disordered in a

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