Reaktion #965

Reaktionsgleichung

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

N-benzyloxycarbonyl-S-methylisothiourea

KHSO4

→

title compound

Ausbeute 67.5%

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

Ausbeute 67.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated to 60°-70° C. for eight hours
2. 2
   Waschenthe 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
   Sonstigewas removed
5. 5
   Extraktionextracted four times with CH2 Cl2
6. 6
   TrocknenThe combined organic layer was dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

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.

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