反応式
[H-].[Na+].C(OC([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)=O)(C)(C)C.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>C1COCC1>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:18][CH2:17][CH2:16][CH:13]2[CH2:12][CH2:11][NH:10][CH2:15][CH2:14]2)=[CH:22][CH:23]=1参加物
実験手順
NaH (60% dispersion in oil, 98 mg, 2.4 mmol, 1.2 equiv.) was added to a solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperidine (468 mg, 2.0 mmol) in THF (10 mL) at 0° C. under Ar protection. The mixture was warmed to room temperature and stirred at that temperature for 3 h. 1-(Bromomethyl)-4-methoxybenzene (353 μL, 2.4 mmol, 1.2 equiv.) was added at room temperature. After stirring for 20 h, the reaction was quenched with saturated aqueous NH4Cl solution. The mixture was extracted three times with EtOAc, and the combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed, and the residue was purified by CC (SiO2, hexane/EtOAc 10:1 to 4:1) to afford the product (268 mg, 38%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.22 (d, 2H, J=8.4 Hz), 6.85 (d, 2H, J=8.8 Hz), 4.40 (s, 2H), 4.05 (m, 2H), 3.76 (m, 4H), 3.45 (t, 2H, J=6.0 Hz), 2.65 (m, 2H), 1.62-1.50 (m, 5H), 1.44 (s, 9H), 1.08 (m, 2H).
後処理
- stirringAfter stirring for 20 h
- customthe reaction was quenched with saturated aqueous NH4Cl solution
- extractionThe mixture was extracted three times with EtOAc
- washthe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customThe solvent was removed
- customthe residue was purified by CC (SiO2, hexane/EtOAc 10:1 to 4:1)
出典と根拠
- ORDレコード
- ord-44d972a8dfec4b2db08071833c126c58
- 出典データセット
- uspto-grants-2013_05
- 特許番号
- US08445684B2
関連ノート
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