Isopropyl iodide → HCID 66876886、化合物

HRID 1666418ノート

反応式

HRID 1666418 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[CH:29](I)([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1)([CH3:31])[CH3:30]

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

生成物 1

HCID 66876886HCID 66876886、化合物収率 75.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.56 mmol) in acetone (5 mL) cooled to 0° C. was added isopropyliodide (0.33 g, 1.96 mmol) and K2CO3 (0.43 g, 3.12 mmol). The reaction mixture was stirred at 80° C. overnight. The reaction mixture was evaporated to dryness and water (10 mL) was added and the mixture was extracted with ethyl acetate three times. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexane) to give the title compound (0.5 g, 75%). 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=3.3 Hz, 1H), 7.28 (m, 2H), 6.96 (d, J=7.5 Hz, 1H), 6.91 (m, 2H), 6.84 (d, J=8.5 Hz, 1H), 6.32 (s, 1H), 4.45 (m, 1H), 3.49 (m, 2H), 3.38 (m, 2H), 2.45 (m, 2H), 2.31 (m, 2H), 1.47 (s, 9H), 1.33 (d, J=6 Hz, 6H); m/z (425.2, M+ H+).

後処理

  1. customThe reaction mixture was evaporated to dryness and water (10 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate three times
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:19 acetone:hexane)

出典と根拠

ORDレコード
ord-d4df9589f6104204a37796e0401e303a
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

読み込み中…