Ammonium Chloride → 2-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanol

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Reaction Conditions

Reaction Steps

To a solution of 4-[(6-bromopyridin-2-yl)methyl]morpholine (Example 2, Step 1) (500 mg, 1.945 mmol) in tetrahydrofuran at −78° C. was added a solution of LDA (1.8 M in tetrahydrofuran/heptane/ethylbenzene, 3.24 ml, 5.83 mmol) over 15 minutes. The resulting red solution was stirred at −78° C. for one hour and then a solution of 1H-1,2,3-benzotriazol-1-ylmethanol (580 mg, 3.89 mmol) in 14 mL tetrahydrofuran was added. After 2.5 hours, a saturated aqueous ammonium chloride solution (5 mL) was added and the reaction mixture was allowed to warm to room temperature. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL), dried with sodium sulfate, filtered, and concentrated. The resulting oil was dissolved in tetrahydrofuran (15 mL) and diethyl ether (30 mL), and this solution was washed with aqueous sodium hydroxide (5 M, 15 mL), brine (15 mL), saturated aqueous sodium carbonate (10 mL), and brine (10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The resulting material was purified by silica gel chromatography (0.2-10% methanol/ethyl acetate) which afforded the title compound. LRMS (APCI) calc'd for C11H15BrN2O2 [M+H]+: 287, Found: 287.

Provenance & Evidence