反応式
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[N:3]1[CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.Cl>C1(C)C=CC=CC=1.CO>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][S:18][CH2:17][CH2:16][N:3]1[C:2](=[O:1])[CH2:6][CH2:5][C@@H:4]1/[CH:7]=[CH:8]/[C@@H:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -30 °C
実験手順
A solution of methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl]pyrrolidin-1-yl}ethyl)thio]-butanoate (0.039 g, 0.1 mmol) in 2 mL of anhydrous toluene was added dropwise to a −30° C. solution of (R)-2-methyl-CBS-oxazaborolidine (1 M in toluene, 0.05 mL, 0.05 mmol) and borane-methyl sulfide complex (10 M, 0.01 mL, 0.1 mmol). The reaction was stirred for 7 hours at −30° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via chromatography yielding 11 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester as an oil. This was taken directly on to the next step.
後処理
- temperatureThe solution was warmed to room temperature
- customthe solvents were removed via reduced pressure
- customThe crude residue was purified via chromatography
出典と根拠
- ORDレコード
- ord-8aa5e02b8b4542b18d3d5fa4e489be9c
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06849657B2
関連ノート
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