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

HRID 273187노트

반응식

HRID 273187 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-3b31c9d39aee423b877ab9bdbfc67daf
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456211B2

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