Ammonium Hydroxide → HCID 9989434、化合物

HRID 2079462ノート

反応式

HRID 2079462 の反応式
[CH:1]1([C:9]([OH:11])=O)[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.C(N1C=CN=C1)([N:14]1C=CN=C1)=O.[OH-].[NH4+]>C(OCC)(=O)C>[CH:1]1([C:9]([NH2:14])=[O:11])[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 10441897Spiro(2.5)octane-1-carboxylic Acid

生成物 1

HCID 9989434HCID 9989434、化合物収率 108.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

A 100 mL flask was charged with the product from Example 1B (2.8 g, 18 mmol), 1,1′-carbonyldiimidazole (2.9 g, 18 mmol) and ethyl acetate (20 mL). The mixture was stirred under nitrogen at ambient temperature for 4 hours, then 20 mL of concentrated ammonium hydroxide was added and the mixture stirred for 18 hours. The mixture was diluted with ethyl acetate (50 mL) and the layers were separated. The organic extract was washed with water (3×15 mL), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was treated with carbon and recrystallized from aqueous methanol to provide the title compound as white crystals (3 g, 78% yield). 1H NMR (CDCl3, 300 MHz) δ 5.55 (s, 2H), 1.3-1.7 (m, 10H), 1.28 (dd, 1H), 1.11 (t, 1H), 0.75 (dd, 1H); 13C NMR (CDCl3, 100 MHz) δ 174.1, 37.6, 28.9, 28.6, 27.5, 26.2, 25.8, 25.6, 19.4; MS m/z 154 (M+H)+.

後処理

  1. stirringthe mixture stirred for 18 hours
  2. customthe layers were separated
  3. extractionThe organic extract
  4. washwas washed with water (3×15 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe crude product was treated with carbon
  8. customrecrystallized from aqueous methanol

出典と根拠

ORDレコード
ord-aa0eb34e98ae4e85b01a347909369313
出典データセット
uspto-grants-2011_04
特許番号
US07932245B2

反応ノート

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