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

HRID 385793Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH:23](=[O:27])[CH:24]([CH3:26])[CH3:25]>O1CCCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[CH:23]([OH:27])[CH:24]([CH3:26])[CH3:25])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

stirringthe reaction was then stirred at −78° C. for 2 hours
customThe reaction was quenched with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via flash chromatography (silica, 50-100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-ca8c4861a53b455490012cf2b8a36a04
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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