Ammonium Hydroxide → HCID 9989434, 화합물

HRID 2079462노트

반응식

HRID 2079462 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 9989434HCID 9989434, 화합물수율 108.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-aa0eb34e98ae4e85b01a347909369313
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932245B2

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