Water → 1-Azabicyclo[2.2.2]octane-2-methanol

HRID 744111노트

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HRID 744111 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][CH:8]2[C:15](O)=[O:16].O.[OH-].[Na+]>C1COCC1>[OH:16][CH2:15][CH:8]1[CH2:9][CH:10]2[CH2:13][CH2:14][N:7]1[CH2:12][CH2:11]2

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 122169671-Azabicyclo(2.2.2)octane-2-carboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 1137841-Azabicyclo[2.2.2]octane-2-methanol수율 120.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Lithium aluminum hydride (0.1 mol, 3.9 g) was suspended in THF (200mL) in a 50 mL flask at 0° C. (VI) (0.03 mol, 5.76g) was added in small portions. After the addition, the reagents were refluxed under a nitrogen atmosphere for 12 hours, cooled to 0° C. followed by dropwise addition of water (3.8 mL) and NaOH (3.9 mL of a 15% aqueous solution). After stirring for 30 minutes, water (12 mL) was added to the reaction mixture followed by additional stirring for 30 minutes. The reaction mixture was filtered, and hot THF was used for additional washings of the precipitate. The filtrate obtained was dried over anhydrous potassium carbonate and filtered again. Removal of THF on a rotary evaporator yielded (VII) as a colorless oil (5.1 g). Distillation at 0.3 mm Hg yielded (VII) (2.75 g) as a clear oil.

후처리

  1. additionAfter the addition
  2. temperaturethe reagents were refluxed under a nitrogen atmosphere for 12 hours
  3. stirringby additional stirring for 30 minutes
  4. filtrationThe reaction mixture was filtered
  5. customThe filtrate obtained
  6. dry with materialwas dried over anhydrous potassium carbonate
  7. filtrationfiltered again
  8. customRemoval of THF
  9. customon a rotary evaporator

출처 및 근거

ORD 기록
ord-63f656116de247d28f010f10452b4479
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559124

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