Sodium Hydroxide → 8-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-8-ol

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Reaction Steps

(S)-1-(4-Bromo-phenyl)-ethylamine (2.68 g), sodium triacetoxyborohydride (2.84 g), and acetic acid (0.77 mL) are added in the given order to a solution of (8-hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-acetaldehyde (7.86 g) in tetrahydrofuran (150 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water (100 mL) and 1 M aqueous NaOH solution (100 mL) are then added and the mixture is stirred for another 20 min. The mixture is extracted with ethyl acetate, and the combined extracts are washed with water and brine. After drying (MgSO4), the solvent is evaporated to give the crude title compound that is used without further purification. Yield: 2.91 g (crude); LC (method 3): tR=2.00 min; Mass spectrum (ESI+): m/z=384/386 (Br) [M+H]+.

Provenance & Evidence