反应 #40342

反应方程式

potassium tert-butylate

5-(benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid

hydrochloric acid

→

desired title compound

收率 45.0%

1-benzyl-azepan-3-one

收率 45.0%

溶剂

toluene

toluene

反应条件

后处理

1. 1
   温度is refluxed for 10 min
2. 2
   workup.ADDITIONthe addition
3. 3
   温度is refluxed for another 1.5 hours
4. 4
   workup.ADDITIONis added
5. 5
   其他The organic phase is separated off
6. 6
   洗涤washed with 25% hydrochloric acid (4×1 ml)
7. 7
   温度The combined hydrochloric-acid aqueous phases are then refluxed for 5 hours
8. 8
   萃取with 2N caustic soda solution and extraction
9. 9
   浓缩The combined organic phases are concentrated by evaporation
10. 10
    干燥after drying over sodium sulphate
11. 11
    其他The obtained residue produces

实验过程

A suspension of potassium tert-butylate (336 mg) in toluene (2.5 ml) is refluxed for 10 min. Then 5-(benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid (695 mg) in toluene (1 ml) is slowly added to the suspension and when the addition is complete the mixture is refluxed for another 1.5 hours. After cooling to room temperature 25% hydrochloric acid (1 ml) is added. The organic phase is separated off and washed with 25% hydrochloric acid (4×1 ml). The combined hydrochloric-acid aqueous phases are then refluxed for 5 hours. After cooling to room temperature the solution is made alkaline (pH 11) with 2N caustic soda solution and extraction is carried out with ethyl acetate. The combined organic phases are concentrated by evaporation after drying over sodium sulphate. The obtained residue produces, after chromatography using silica gel (ethyl acetate/heptane 1:5) the desired title compound (197 mg) in a yield of 45% (Bull. Chem. Soc. Jpn. 1956, 29, 631-632; DE2206385).

来源