Hydrochloric Acid → (S)-N-[2-[7-Allyl-5-bromo-2,3-dihydro-6-hydroxy-1H-inden-1-YL]ethyl]propanamide
反応式
C([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C@H:11]2[CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:7][C:6]=1[Br:21])C=C.O.Cl.C(OCC)(=O)C.C(N(CC)[C:33]1[CH:38]=CC=C[CH:34]=1)C>>[CH2:38]([C:13]1[C:5]([OH:4])=[C:6]([Br:21])[CH:7]=[C:8]2[C:12]=1[C@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:33]=[CH2:34]参加物
反応条件
- 温度
- 202.5 °C
実験手順
A suspension of (S)-N-[2-(6-allyloxy-5-bromoindan-1-yl)ethyl]propionamide (50.75 g, 144 mmol.) in N,N-diethylaniline (150 mL) was stirred for 2.5 hours at 200-205° C. under argon atmosphere. The reaction mixture was cooled, followed by distilling off N,N-diethylaniline under reduced pressure to leave an oily residue. To the residue were added water (50 mL), 2N HCl (50 mL) and ethyl acetate (100 mL). The mixture was subjected to extraction twice to extract the organic matter. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=7:3) to afford the title compound (yield 40.6 g, 80%).
後処理
- temperatureThe reaction mixture was cooled
- distillationby distilling off N,N-diethylaniline under reduced pressure
- customto leave an oily residue
- extractionThe mixture was subjected to extraction twice
- extractionto extract the organic matter
- washThe extract solution was washed with a saturated aqueous saline solution and water, which
- dry with materialwas then dried over anhydrous magnesium sulfate
- distillationby distilling off the solvent under reduced pressure
- customThe residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=7:3)
出典と根拠
- ORDレコード
- ord-5fcc2ba1537b4dffa5ae4850320b49ce
- 出典データセット
- uspto-grants-2000_03
- 特許番号
- US06034239
反応ノート
読み込み中…