反应 #806309

反应方程式

2-amino-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

lithium

→

1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine

溶剂

diethyl ether

diethyl ether

反应条件

后处理

1. 1
   workup.ADDITIONAt the end of addition
2. 2
   其他the icebath was removed
3. 3
   温度The reaction mixture was cooled to 0° C.
4. 4
   workup.ADDITIONaqueous solution of sodium chloride was added
5. 5
   其他to quench the excess lithium aluminumhydride
6. 6
   workup.ADDITIONSodium hydroxide solution was added
7. 7
   workup.STIRRINGthe biphasic mixture was stirred for 1 h
8. 8
   萃取The product was extracted with diethyl ether (3×30 mL)
9. 9
   洗涤The ethereal extracts were washed with brine
10. 10
    干燥dried over anhydrous sodium sulfate
11. 11
    其他Evaporation of the solvent

实验过程

A solution of 2-amino-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (420 mg, 1.567 mmol) in diethyl ether (3 mL) was added dropwise to a slurry mixture of lithium aluminumhydride (307 mg, 7.835 mmol) in diethyl ether (30 mL) cooled to 0° C. At the end of addition, the icebath was removed and the reaction was stirred at room temperature for 3 h. The reaction mixture was cooled to 0° C. and aqueous solution of sodium chloride was added to quench the excess lithium aluminumhydride. Sodium hydroxide solution was added and the biphasic mixture was stirred for 1 h. The product was extracted with diethyl ether (3×30 mL). The ethereal extracts were washed with brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine as yellow oil (362.7 mg, 96%, 4.3:1.0 ratio of cis:trans). The crude product was used without further purification.

来源