反応式
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:17].[Na+]>CO>[CH3:10][C:6]1[N:5]=[C:4]([CH:1]([NH2:17])[CH3:2])[CH:9]=[CH:8][CH:7]=1参加物
実験手順
To a solution of 2-acetyl-6-methylpyridine (4.7 g, 34.8 mmol) in anhydrous methanol (100 ml) was added ammonium acetate (26.8 g, 348 mmol) and sodium cyanoborohydride (1.75 g, 27.8 mmol) and the resulting mixture stirred at RT overnight. The mixture was evaporated and the residue dissolved in water and basified by the addition of KOH and extracted with DCM (×3). The DCM layers were combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica to afford the title compound (i-14) (eluent: 5% MeOH in DCM) to give 2.8 g (59%) as a clear oil. 1H NMR (CDCl3): 1.41 (d, J6.7 Hz, 3H), 1.78 (brs, 2H), 2.54 (s, 3H), 4.21 (q, J6.7 Hz, 1H), 6.99 (d, J7.6 Hz, 1H), 7.09 (d, J7.7 Hz, 1H), 7.52 (m, 1H).
後処理
- customThe mixture was evaporated
- dissolutionthe residue dissolved in water
- additionbasified by the addition of KOH
- extractionextracted with DCM (×3)
- washwashed with sat. NaCl
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography on silica
出典と根拠
- ORDレコード
- ord-432d3a96c8bb4918869b477997b70078
- 出典データセット
- uspto-grants-2013_12
- 特許番号
- US08604038B2
関連ノート
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