Reaktion #1672676

Reaktionsgleichung

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

N-benzyloxycarbonyl-S-methylisothiourea

KHSO4

→

title compound

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe water layer was washed with a mixture of the toluene and ethyl acetate
2. 2
   workup.WAITleft for 2 days under which time the Boc group
3. 3
   Sonstigewas removed
4. 4
   Extraktionextracted four times with CH2Cl2The combined organic layer
5. 5
   Trocknenwas dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

2.18 g (0.0102 mmole) (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. 0.3 M 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 CH2Cl2The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound.

Quelle