Water → tert-Butyl (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

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Reaction Steps

To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-yl-carbamate (2.7 g, 10.9 mmol), prepared as described in Example 1A, in THF (50 mL) at RT was added dropwise a solution of pyridinium tribromide (3.83 g, 0.41 mmol) in THF (50 mL). After addition, the reaction mixture was stirred for 15 min, then water (60 mL) and ether (60 mL) added. The aqueous layer was separated, and extracted with EtOAc (2×50 mL). The combined organics were washed with saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 50%) in hexanes to give the title compound (2.5 g, 70% yield) as a white solid.

Provenance & Evidence