Water → 8-(5-Bromo-4-(4-chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane

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Reaction Steps

To a stirred solution of 8-(4-(4-chlorophenyl)thiazol-2-yl)-3-oxa-8-azabicyclo[3.2.1]octane (Step-2 of compound 56, 0.27 g, 0.88 mmol) in DMF (5 ml) at 0° C. was added N-bromosuccinimide (0.19 g, 1.06 mmol) in a portion wise manner. The resulting mixture was stirred at room temperature for 30 min. The progress of reaction was monitored by TLC. To the reaction mixture water (20 ml) and 1M NaOH solution (5 ml) were added slowly and aqueous layer was extracted with ethyl acetate (2×30 ml). The reaction mixture was washed with water (1×20 ml). The combined organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 10% ethyl acetate in hexanes as an eluent to obtain the title compound (0.26 g, 78.0%). MS: m/z 386 (M+1).

Provenance & Evidence