Réaction #959

Équation de réaction

methanesulphonyl chloride

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

triethylamine

→

title compound

Rendement 50.0%

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

Rendement 50.0%

Solvants

diethyl ether

diethyl ether CH2Cl2

ethyl acetate heptane

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   Extractionextracted with a 0.3M KHSO4 -solution
4. 4
   LavageThe water layer was washed once with CH2Cl2
5. 5
   Extractionextracted twice with CH2Cl2
6. 6
   AutreThe combined organic layer was dried (Na2 SO4)
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated

Mode opératoire

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.

Source