Isobutyraldehyde → 1-(6-Bromopyridin-2-yl)-3-methyl-1-morpholin-4-ylbutan-2-ol

Participants

Reaction Conditions

Reaction Steps

4-[(6-Bromopyridin-2-yl)methyl]morpholine (Example 45, Step 1) (500 mg, 1.95 mmol) was placed under argon and then taken up in tetrahydrofuran (19.5 mL). The solution was cooled to −78° C. LDA (1.62 mL of 1.8 M, 2.92 mmol) was added dropwise over 30 minutes. The mixture was stirred at −78° C. for one hour. Isobutyraldehyde (0.71 mL, 7.8 mmol) was then added and the reaction was then stirred at −78° C. for 2 hours. 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 via flash chromatography (silica, 50-100% ethyl acetate/hexanes) afforded the title compound as a white solid.

Provenance & Evidence