Potassium bisulfate → benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 341808

Reaktionsgleichung

Reaktionsgleichung von HRID 341808
C(OC([NH:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=O)(C)(C)C.[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]([NH:26][C:27]([N:13]1[CH2:14][CH2:15][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:12]1)=[NH:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 516920Potassium bisulfateHCID 21955469tert-butyl N-[2-(pyrrolidin-3-yl)ethyl]carbamateHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

Produkt 1

HCID 140379083benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamateAusbeute 67.529,203 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  1. temperatureheated to 60°-70° C. for eight hours
  2. washthe water layer was washed with a mixture of the toluene and ethyl acetate
  3. waitleft for 2 days under which time the Boc group
  4. customwas removed
  5. extractionextracted four times with CH2Cl2The combined organic layer
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-61172809add7487dba30b6f3d3ca4556
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856307

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