Aluminium lithium hydride → HCID 58724165、化合物
反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2([C:21](OCC)=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2([CH2:21][OH:22])[CH2:20][CH2:19][CH2:18]2)[CH2:15][CH2:16]1)(=[O:9])=[O:10]参加物
4
反応条件
- 温度
- 0 °C
実験手順
Ethyl 1-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)cyclobutanecarboxylate was dissolved in THF (1 ml). Lithium aluminum hydride (0.5 ml, 1.0 M in THF) was added at 0° C. The reaction mixture was stirred at 0° C. for 45 minutes. It was quenched by careful addition of H2O at 0° C. The mixture was stirred for another 30 minutes before 1N NaOH and equal volume of brine were added. The mixture was extracted with EtOAc three times. Combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, 7% MeOH/CH2Cl2) to give the title compound (20 mg, 8% 3 steps) as a white solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm: 1.38-1.48 (m, 1 H), 1.67-1.78 (m, 1 H), 1.80-1.89 (m, 1 H), 1.91-2.00 (m, 1 H), 2.34-2.51 (m, 4 H), 2.56-2.68 (m, 2 H), 2.64 (bs, 1 H), 3.28-3.31 (m, 4 H), 3.57 (ddd, J=16.8, 10.9, 5.9 Hz, 2 H), 7.36-7.41 (m, 1 H), 7.45-7.53 (m, 2 H), 8.01 (dd, J=7.8, 1.5 Hz, 1 H); ESI-MS: m/z 345.3 (M+H)+.