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

HRID 744111ノート

反応式

HRID 744111 の反応式
[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

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 122169671-Azabicyclo(2.2.2)octane-2-carboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 1137841-Azabicyclo[2.2.2]octane-2-methanol収率 120.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-63f656116de247d28f010f10452b4479
出典データセット
uspto-grants-1996_09
特許番号
US05559124

反応ノート

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