反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C([Li])CCC.[C:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].S([O-])(O)(=O)=O.[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCCCCC>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([C:26]2([OH:29])[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:28][CH2:27]2)[CH:7]=1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -70 °C
実験手順
To a stirred solution of 2-bromo-4-chloroanisole (164 g, 0.74 mol) in tetrahydrofuran (1 L), cooled at −70° C. and under an atmosphere of argon, was added butyl lithium (2.7 M in heptane, 280 ml) over a period of 1 hour. The mixture was stirred for 30 minutes, maintaining the temperature at −70° C., before the addition of N-boc-4-piperidone (145 g, 0.73 mol) in tetrahydrofuran (250 ml) over a period of 1 hour. The reaction temperature was warmed to −40° C. over 2 hours before the addition of sodium hydrogen sulphate (5M aqueous, 160 ml), sodium sulphate (300 g) and hexane (500 ml). The mixture was stirred for 10 hours. The organic layer was decanted, filtered through silica gel (300 g, 63/100 μm) washing with ethyl acetate:hexane (4:6, by volume, 2×400 ml). The filtrate was evaporated in vacuo and the residue recrystallized from ethyl acetate:hexane to afford the title compound as white crystals, 100 g, 39% yield.
後処理
- stirringThe mixture was stirred for 10 hours
- customThe organic layer was decanted
- filtrationfiltered through silica gel (300 g, 63/100 μm)
- washwashing with ethyl acetate:hexane (4:6, by volume, 2×400 ml)
- customThe filtrate was evaporated in vacuo
- customthe residue recrystallized from ethyl acetate
出典と根拠
- ORDレコード
- ord-b547530a686e4e11ad75cb3f5b5eb618
- 出典データセット
- uspto-grants-2014_12
- 特許番号
- US08907101B2
関連ノート
読み込み中…