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

HRID 744111Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-63f656116de247d28f010f10452b4479
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559124

Reaction notes

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