反応 #76780

反応方程式

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

溶媒

water

THF

THF

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for an additional 15 minutes
3. 3
   温度to warm to 0° C. over 1 hour
4. 4
   抽出the solution was extracted twice with chloroform
5. 5
   洗浄the combined extracts were washed once with brine
6. 6
   乾燥The resulting solution was dried over MgSO4
7. 7
   ろ過filtered
8. 8
   その他evaporated in vacuo

実験手順

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.

出典