Aluminium lithium hydride → 3-Hexyl-6-methyl-6-[3-(2-thienyl)phenyl]-3-azabicyclo[3.1.0]hexane

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Reaction Steps

3-Hexyl-6-methyl-6-[3-(2-thienyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 69, 64 mg, 0.19 mmol) was dissolved in tetrahydrofuran (20 ml) at 0° C. Lithium aluminium hydride (1M in tetrahydrofuran, 0.4 ml, 0.4 mmol) was added under nitrogen and then the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched by adding aqueous sodium hydroxide solution (2N, 0.8 ml), followed by solid sodium hydrogen carbonate and ethyl acetate. The reaction mixture was stirred vigorously and then filtered through Celite®. The filtrate was concentrated in vacuo and the residue chromatographed on silica gel eluting the product with hexane:ethyl acetate (2:1) as a colourless oil (66 mg, 64%).

Provenance & Evidence