1,1'-Carbonyldiimidazole → HCID 90253492, 화합물

HRID 1478768노트

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HRID 1478768 반응식
[CH3:1][C@@H:2]1[CH2:4][C@H:3]1[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:21][NH:22][O:23][CH3:24]>ClCCl>[CH3:24][O:23][N:22]([CH3:21])[C:5]([C@@H:3]1[CH2:4][C@H:2]1[CH3:1])=[O:7]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 6995705rel-(1R,2R)-2-Methylcyclopropanecarboxylic acid

생성물 1

HCID 90253492HCID 90253492, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

To a solution of (1R,2R)-2-methylcyclopropanecarboxylic acid (44 g, 0.44 mol) in dichloromethane (600 mL) was added 1,1′-carbonyldiimidazole (79 g, 0.45 mol) portion-wise at 20° C. The reaction was stirred at 25° C. for 2 hours. N,O-Dimethylhydroxylamine hydrochloride (52 g, 0.53 mol) was added portion-wise and stirring was continued at 25° C. for 16 hours. The reaction mixture was washed with water (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (Gradient: 2% to 20% ethyl acetate in petroleum ether) provided the product as a colorless oil. Yield: 52 g, 363 mmol, 82%. 1H NMR (400 MHz, CDCl3) δ 3.74 (s, 3H), 3.19 (s, 3H), 1.80-1.86 (m, 1H), 1.30-1.38 (m, 1H), 1.17 (dt, J=8.5, 4.3 Hz, 1H), 1.12 (d, J=6 Hz, 3H), 0.64 (ddd, J=8.2, 6.1, 3.8 Hz, 1H).

후처리

  1. stirringstirring
  2. waitwas continued at 25° C. for 16 hours
  3. washThe reaction mixture was washed with water (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-253c93fa481640c6968e14409fc2e17f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403846B2

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