Acetaldehyde → 1-(6-Bromopyridin-2-yl)-1-morpholin-4-ylpropan-2-ol

Participants

Reaction Conditions

Reaction Steps

4-[(6-Bromopyridin-2-yl)methyl]morpholine (Example 45, step 1) (200 mg, 0.78 mmol) was placed under argon and then taken up in tetrahydrofuran (8 mL). The solution was cooled to −78° C. followed by the addition of LDA (0.65 mL of 1.8 M, 1.17 mmol) over 30 minutes. The reaction was maintained at −78° C. for one hour. Acetaldehyde (0.1 mL, 7.8 mmol) was then added and the reaction was then stirred at −78° C. for 2 hours. An additional portion of acetaldehyde (0.1 mL, 7.8 mmol) was then added and the reaction was then stirred an additional 2 hrs at −78° C. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification of the crude mixture via flash chromatography (silica, 0-5% methanol/ethyl acetate) afforded the title compound as a white solid.

Provenance & Evidence