Reacción #965

Ecuación de reacción

(3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine

N-benzyloxycarbonyl-S-methylisothiourea

KHSO4

→

title compound

Rendimiento 67.5%

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

Rendimiento 67.5%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated to 60°-70° C. for eight hours
2. 2
   Lavadothe water layer was washed with a mixture of the toluene and ethyl acetate
3. 3
   workup.WAITleft for 2 days under which time the Boc group
4. 4
   Otrowas removed
5. 5
   Extracciónextracted four times with CH2 Cl2
6. 6
   SecadoThe combined organic layer was dried (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated

Procedimiento

2.18 g (0.0102 mole) (3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60°-70° C. for eight hours followed by stirring at room temperature for one day. 0.3M KHSO4 -solution was added and the water layer was washed with a mixture of the toluene and ethyl acetate and left for 2 days under which time the Boc group was removed. The acidic water phase was made alkaline and extracted four times with CH2 Cl2. The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound.

Fuente