93273-57-5Relevant articles and documents
Studies on Antifertility Agents: Part XLII - Synthesis and Antifertility Study of 6-Methoxy-3-phenyl-1-tetralin
Malik, Mangel S.,Rastogi, Shri Nivas
, p. 834 - 838 (2007/10/02)
LAH reduction of methyl β-(m-methoxyphenyl)-α-phenylpropionate (2) gives propanol 3 which after treatmeant with p-TsCl is reacted with KCN to yield the butyronitrile (5) and a mixture of isomeric propenes (6).Alkaline hydrolysis of 5 gives 7 which on cyclisation with PCl5-SnCl4 affords 6-methoxy-3-phenyl-1-tetralone (8).Reaction of Me2N(CH2)3MgCl with 8 furnishes the corresponding 1-substituted dihydronaphthalene (12).KBH4 reduction of 8 gives preferably 1,3-cis-tetralol (9a) as indicated by 13C-NMR and PMR data, NOE results and also by 13C-NMR data of its acetyl derivative (10). Condensation of 9a with PhOH-AlCl3 gives a mixture of products from which cis/trans-mixture of 1-(p-hydroxyphenyl) (13) and 1-(o-hydroxyphenyl) (14) derivatives and dialin (15) are obtained.Acetylation of 13 (a mixture of two isomers in 55:45 proportion as shown by GLC) and 14 with Ac2O-pyridine gives the corresponding acetoxy derivatives (16 and 17).Compound 13 on condensation with β-chloroethylpyrrolidine affords the title compound (18).In female albino rats, compound 18 does not prevent pregnancy at 10 mg/kg dose.As 18 is a mixture no inference can be had about the receptor site.
