反应 #321856

反应方程式

3-pyrrolidinacetic acid methyl ester

3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propanol

triethylamine

Triethylamine

Methanesulfonyl chloride

→

1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acid methyl ester

收率 30.1%

溶剂

THF

反应条件

后处理

1. 1
   workup.ADDITIONwhen addition
2. 2
   过滤The mixture was filtered
3. 3
   温度The mixture was heated
4. 4
   温度at reflux temperature for 4 h
5. 5
   workup.STIRRINGstirred at room temperature for 48 h
6. 6
   温度the mixture was heated
7. 7
   温度at reflux temperature for 24 h
8. 8
   其他was removed by evaporation in vacuo
9. 9
   其他The residue was purified by column chromatography on silica gel (125 g)
10. 10
    workup.ADDITIONa mixture of dichloromethane and methanol (9:1) as eluent

实验过程

3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propanol (2.0 g, 0.0079 mol, prepared as described in example 10) was dissolved in dry THF (25 ml) under an atmosphere of nitrogen, and triethylamine (2.75 ml) was added. Methanesulfonyl chloride (0.61 ml, 0.0079 mol) was added dropwise and when addition was complete the reaction mixture was stirred for 45 minutes. The mixture was filtered and 3-pyrrolidinacetic acid methyl ester (2.4 g, 0.012 mol) was added to the filtrate. The mixture was heated at reflux temperature for 4 h and then stirred at room temperature for 48 h. Triethylamine (2.2 ml) was added and the mixture was heated at reflux temperature for 24 h. After cooling to room temperature the solvent was removed by evaporation in vacuo. The residue was purified by column chromatography on silica gel (125 g) using a mixture of dichloromethane and methanol (9:1) as eluent, affording 0.9 g (27%) of 1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-3-pyrrolidinacetic acid methyl ester as an oil. Rf : 0.15 (SiO2 ; dichloromethane/methanol/acetic acid=20:2:1).

来源