反応式
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]([OH:18])[CH2:15][CH:16]=[CH2:17])[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]([O:18][CH2:25][CH:24]=[CH2:23])[CH2:15][CH:16]=[CH2:17])[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
(S)-4-(2-Hydroxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.54 g, 8.91 mmol) was dissolved in dry tetrahydrofuran (60 mL). Sodium hydride (60% suspension in mineral oil, 360 mg) was added. The mixture was stirred at 0° C. for 5 min. Then allylbromide (1.60 mL) was added. The mixture was stirred at room temperature for 18 h. Solvents were evaporated and the residue was extracted with diethyl ether and citric acid solution. The organic layer was washed with saturated sodium chloride solution and concentrated. The crude material was purified through flash column chromatography (silica gel, 5-30% ethyl acetate/hexanes) to afford (S)-4-(2-allyloxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.38 g, 48% yield for two steps) as an oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 12H), 1.56, 1.60 (2×s, 3H), 1.64-1.77 (m, 1H), 1.80-2.07 (m, 1H), 2.32 (br. s., 2H), 3.48 (br. s., 1H), 3.79-4.23 (m, 5H), 4.98-5.19 (m, 3H), 5.26 (d, J=17.2 Hz, 1H), 5.72-5.98 (m, 2H).
後処理
- stirringThe mixture was stirred at room temperature for 18 h
- customSolvents were evaporated
- extractionthe residue was extracted with diethyl ether and citric acid solution
- washThe organic layer was washed with saturated sodium chloride solution
- concentrationconcentrated
- customThe crude material was purified through flash column chromatography (silica gel, 5-30% ethyl acetate/hexanes)
出典と根拠
- ORDレコード
- ord-97ccc01948ed4c0bacb054209452f9af
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07741327B2
関連ノート
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