反応 #959

反応方程式

methanesulphonyl chloride

(3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethyl pyrrolidine

triethylamine

→

title compound

収率 50.0%

(3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine

収率 50.0%

溶媒

diethyl ether

diethyl ether CH2Cl2

ethyl acetate heptane

反応条件

後処理

1. 1
   その他The solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   抽出extracted with a 0.3M KHSO4 -solution
4. 4
   洗浄The water layer was washed once with CH2Cl2
5. 5
   抽出extracted twice with CH2Cl2
6. 6
   その他The combined organic layer was dried (Na2 SO4)
7. 7
   ろ過filtered
8. 8
   その他evaporated

実験手順

0.7 g (2.53 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethyl pyrrolidine and 0.70 ml (5.05 mmole) triethylamine was dissolved in 15 ml diethyl ether/CH2Cl2 1/1 and the mixture was cooled to 0° C. 0.25 ml (3.29 mmole) methanesulphonyl chloride in 3 ml diethyl ether was slowly added and the reaction mixture was stirred at 0° C for three hours. The solvent was evaporated and the residue was dissolved in ethyl acetate and extracted with a 0.3M KHSO4 -solution. The water layer was washed once with CH2Cl2. The water layer was made neutral with 10M NaOH-solution and extracted twice with CH2Cl2. The combined organic layer was dried (Na2 SO4), filtered and evaporated to yield 0.450 g (50%) of the title compound.

出典