Reaktion #76780

Reaktionsgleichung

Quinuclidin-3-one

t-butyl acetate

diisopropylamine

n-butyllithium

→

subtitle compound

2-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic Acid T-butyl ester

Lösungsmittel

water

THF

THF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for an additional 15 minutes
3. 3
   Temperaturto warm to 0° C. over 1 hour
4. 4
   Extraktionthe solution was extracted twice with chloroform
5. 5
   Waschenthe combined extracts were washed once with brine
6. 6
   TrocknenThe resulting solution was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated in vacuo

Vorschrift

To a solution of diisopropylamine (6.7 mL) in tetrahydrofuran (THF) (20 mL) at 0° C. was added n-butyllithium (2.3M in hexanes; 20 mL). The reaction mixture was stirred for 40 minutes and then cooled to −78° C. To this mixture a solution of t-butyl acetate (6.4 mL) in THF (10 mL) was added dropwise and stirring was continued for an additional 15 minutes. Quinuclidin-3-one (5 g) in THF (15 mL) was added to the mixture dropwise and the mixture was allowed to warm to 0° C. over 1 hour. To this solution water (100 mL) was added, the solution was extracted twice with chloroform and the combined extracts were washed once with brine. The resulting solution was dried over MgSO4, filtered, and evaporated in vacuo to give 9.53 g of the subtitle compound as an off-white solid.

Quelle