Sodium Hydroxide → HCID 67996200, compound

Participants

Reaction Steps

(S)-1-(4-Bromo-phenyl)-ethylamine (0.17 mL), sodium triacetoxyborohydride (0.25 g), and acetic acid (0.07 mL) are added in the given order to a solution of [3,3-dimethyl-9-(2-oxo-ethyl)-1,5-dioxa-spiro[5.5]undec-9-yl]acetic acid methyl ester (0.35 g) in tetrahydrofuran (5 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water (5 mL) and 1 M aqueous NaOH solution (5 mL) are then added and the mixture is stirred for another 20 min. The mixture is extracted with tert-butyl methyl ether, and the combined extract is washed with water and brine. After drying (MgSO4), the solvent is evaporated to give an oil that is treated with a mixture of water and ethanol to precipitate the title compound. Yield: 0.29 g (ca. 70% pure); Mass spectrum (ESI+): m/z=450/452 (Br) [m+H]+.

Provenance & Evidence