Реакция #965

Уравнение реакции

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

N-benzyloxycarbonyl-S-methylisothiourea

KHSO4

→

title compound

Выход 67.5%

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

Выход 67.5%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Температураheated to 60°-70° C. for eight hours
2. 2
   Промывкаthe 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
   Другоеwas removed
5. 5
   Экстракцияextracted four times with CH2 Cl2
6. 6
   СушкаThe combined organic layer was dried (Na2SO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated

Методика

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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