Ethyl bromoacetate → HCID 70413007, compound

Participants

Reaction Conditions

Reaction Steps

3-(4'-Fluorophenyl)-3-hydroxy-6-methyl-1-(4-pyridyl)indane (Example 8) (9.0 g) was refluxed with ethyl bromoacetate (5.0 g) in acetone (50 ml) for 3 hrs. The reaction mixture was cooled in a refrigerator overnight and the precipitated pyridinium bromide filtered off. Yield: 7.8 g (56.9%). MP: 177°-78° C. This bromide (7.0 g) was dissolved in methanol (50 ml), cooled to 0° C., and NaBH4 (3.0 g) was added during 1 hour under stirring. The reaction mixture was poured into NH4Cl (10 g) in 1 liter of H2O and finally extracted with ethyl acetate (2×150 ml). The combined organic phases were dried (MgSO4) and the ethyl acetate evaporated. The remaining oil (1-(1-ethylcarboxymethyl-1,2,3,6-tetrahydropyrid-4-yl)-3-(4'-fluorophenyl)-3-hydroxy-6-methylindane) was dissolved in dry tetrahydrofuran (25 ml) and added dropwise to a suspension of LiAlH4 (1.8 g) in dry tetrahydrofuran under ice cooling. The mixture was refluxed for two hours, hydrolysed by careful addition of H2O (5 ml) in tetrahydrofuran (100 ml). The precipitate was filtered off, and the solvent evaporated leaving the title compound as an oil.

Provenance & Evidence