Sodium hydride → (R)-1-(5-Benzyloxypentyl)-4-butylpyrrolidin-2-one

HRID 273187ノート

反応式

HRID 273187 の反応式
[CH2:1]([C@H:5]1[CH2:9][NH:8][C:7](=[O:10])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:8]1[CH2:9][C@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][C:7]1=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 14221121Benzyl 5-Bromoamyl EtherHCID 55287323(R)-4-butylpyrrolidin-2-one

生成物 1

HCID 69310462(R)-1-(5-Benzyloxypentyl)-4-butylpyrrolidin-2-one収率 95%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of (R)-4-butylpyrrolidin-2-one (0.42 g, 2.9 mmol) in dry dimethylformamide (10 mL) under argon was slowly added sodium hydride (60% in mineral oil, 0.14 g, 3.5 mmol) at 0° C. After stirring at 0° C. for 30 minutes, 5-benzyloxypentyl bromide (0.9 g, 3.5 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL). The organic solution was washed with water (4×30 mL) and brine (30 mL), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes) to afford 0.73 g (95%) of (R)-1-(5-benzyloxypentyl)-4-butylpyrrolidin-2-one as a colorless oil: 1H NMR (CDCl3) δ 7.33 (m, 5 H), 4.51 (s, 2 H), 3.45 (m, 3 H), 3.27 (t, 2 H), 2.99 (dd, 1 H), 2.52 (dd, 1 H), 2.32 (m, 1 H), 2.06 (m, 1 H), 1.24-1.71 (m, 12 H), 0.93 (t, 3 H). MS(ES) m/e 318 [M+H]+.

後処理

  1. customat 0° C
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. washThe organic solution was washed with water (4×30 mL) and brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes)

出典と根拠

ORDレコード
ord-3b31c9d39aee423b877ab9bdbfc67daf
出典データセット
uspto-grants-2008_11
特許番号
US07456211B2

反応ノート

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