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monohydrate

By Jiang-sheng Li, A Jim Simpson, B Xiao-jun Li, C Xun Li A, Peng-mian Huang A, Chno Ho and Monoclinic C

Abstract

disorder in main residue; R factor = 0.048; wR factor = 0.114; data-to-parameter ratio = 7.7. In the title compound, C24H39NO2 H2O, the A and C rings of the pregnolene derivative sterol adopt chair conformations, with the B ring in a flattened chair conformation and the fivemembered ring in an envelope conformation twisted about the C/D ring junction. The N-tert-butylcarboxamide substituent is equatorial. The 3-hydroxy H atom and one H atom of the water molecule are disordered over two positions with equal occupancies. In the crystal structure, O—H O hydrogen bonds between the 3-hydroxy groups of neighbouring molecules form dimers in the bc plane and these dimers are stacked along the a axis by additional O—H O hydrogen bonds involving the water molecules. The steric effect of the bulky tert-butyl substituent in the carboxamide chain precludes hydrogen-bond formation by the N—H group. Related literature The title compound is an intermediate in the synthesis of finasteride (Li et al., 2001). For pharmaceutical applications of finasteride, systematic name N-(tert-butyl)-3-oxo-4-aza-5androst-1-ene-17-carboxamide

Year: 2009
OAI identifier: oai:CiteSeerX.psu:10.1.1.352.1126
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