1,1'-Carbonyldiimidazole → HCID 90253492、化合物

HRID 1478768ノート

反応式

HRID 1478768 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 90253492HCID 90253492、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-253c93fa481640c6968e14409fc2e17f
出典データセット
uspto-grants-2016_08
特許番号
US09403846B2

反応ノート

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