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

HRID 869

Reaction equation

HRID 869 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 140379083benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamateYield 67.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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 CH2 Cl2
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d42f48a7d3fc473aba6c5139093935b5
Source dataset
uspto-grants-1998_03
Patent number
US05723444

Linked notes

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