(Bis(2-methoxyethyl)amino)sulfur trifluoride → 1-Piperidinecarboxylic acid, 4-(4-cyanophenyl)-4-fluoro-, 1,1-dimethylethyl ester
反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].COCCN(S(F)(F)[F:33])CCOC>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:33])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]参加物
4
反応条件
- 温度
- -78 °C
実験手順
To a stirred solution of compound 1.2 (5 g, 16.54 mmol, 1.00 equiv) in dichloromethane (250 mL) under nitrogen at −78° C. was added dropwise Deoxo-Fluor® (4.4 g, 19.89 mmol, 1.20 equiv). The resulting mixture was stirred for 1 h at −78° C. The reaction mixture was then carefully quenched by the addition of 50 mL of sodium bicarbonate (aq.sat.) and extracted with 3×100 mL of dichloromethane. The combined organic layers were washed with 150 mL of brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:30) as eluent to yield 2.5 g (35%) of the title compound as a white solid.
後処理
- customThe reaction mixture was then carefully quenched by the addition of 50 mL of sodium bicarbonate (aq.sat.)
- extractionextracted with 3×100 mL of dichloromethane
- washThe combined organic layers were washed with 150 mL of brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified
出典と根拠
- ORDレコード
- ord-0b8aeb7d9af84260a5b2e3a566d8a664
- 出典データセット
- uspto-grants-2014_10
- 特許番号
- US08871790B2
反応ノート
読み込み中…