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Triethylamine → 2,5-Dioxopyrrolidin-1-yl 1-methylcyclopropyl carbonate

HRID 1893657
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HRID 1893657 반응식
[CH3:1][C:2]1([OH:5])[CH2:4][CH2:3]1.[O:6]=[C:7]1[CH2:11][CH2:10][C:9](=[O:12])[N:8]1[O:13][C:14](=O)[O:15]N1C(=O)CCC1=O.C(N(CC)CC)C>C(#N)C.CCOC(C)=O>[CH3:1][C:2]1([O:5][C:14](=[O:15])[O:13][N:8]2[C:9](=[O:12])[CH2:10][CH2:11][C:7]2=[O:6])[CH2:4][CH2:3]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 115644661-Methylcyclopropan-1-ol

생성물 1

HCID 577528092,5-Dioxopyrrolidin-1-yl 1-methylcyclopropyl carbonate수율 19.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate
용매

실험 절차

To a solution of 1-methyl-cyclopropanol (1.25 g, 17.4 mmol) in acetonitrile (44 mL) was added carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester (6.68 g, 26.1 mmol) and triethylamine (7.3 mL, 52.3 mmol). The reaction was stirred at room temperature for 21 h. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 (2×) and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica (15→50%→100% Hex/EtOAc) to provide carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 1-methyl-cyclopropyl ester (722.8 mg, 19%): 1H NMR (CDCl3, 300 MHz) δ 2.83 (s, 4H), 1.63 (s, 3H), 1.10 (m, 2H), 0.73 (m, 2H).

후처리

  1. washwashed with saturated aqueous NaHCO3 (2×) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography on silica (15→50%→100% Hex/EtOAc)

출처 및 근거

ORD 기록
ord-3446924b27624dc7a753ffd3e5934721
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08513186B2

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