反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1.[Li]CCCC.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>O1CCCC1>[CH3:19][N:20]1[CH2:25][CH2:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([CH3:13])[O:12][CH2:11][CH2:10][O:9]3)=[CH:4][N:3]=2)([OH:26])[CH2:22][CH2:21]1参加物
反応条件
- 温度
- -78 °C
実験手順
2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (500 mg, 2.048 mmol) (described in the literature: Bioorg. Med. Chem., 2005, 13, 6763) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to −78° C. under nitrogen. n-BuLi (901.2 μL of 2.5 M, 2.253 mmol) was added dropwise and the reaction mixture was stirred at −78° C. for 30 minutes. 1-Methyl-4-piperidone (602.6 mg, 655.0 μL, 5.325 mmol) was added and the reaction was allowed to stir at −78° C. for 20 minutes then warmed slowly to ambient temperature. The reaction mixture was stirred at room temperature for 18 hours and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a sticky orange solid (483.4 mg, 85% yield).
後処理
- stirringto stir at −78° C. for 20 minutes
- temperaturethen warmed slowly to ambient temperature
- stirringThe reaction mixture was stirred at room temperature for 18 hours
- concentrationconcentrated in vacuo
- customThe residue was purified on silica gel by flash column chromatography
出典と根拠
- ORDレコード
- ord-3a09eb135c464493bad342fe7685d6d6
- 出典データセット
- uspto-grants-2015_02
- 特許番号
- US08962642B2
関連ノート
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