(Pyrrolidin-3-yl)methanol → benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 862

Reaktionsgleichung

Reaktionsgleichung von HRID 862
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:8]([O:15][C:16]([NH:18][C:19](=[NH:22])OC)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:16]([NH:18][C:19]([N:5]1[CH2:6][CH2:7][CH:3]([CH2:2][OH:1])[CH2:4]1)=[NH:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 13400657(Pyrrolidin-3-yl)methanolHCID 139267837benzyl N-(C-methoxycarbonimidoyl)carbamate

Produkt 1

HCID 140379085benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamateAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1.01 g (0.01 mole) (3RS)-3-hydroxymethyl pyrrolidine and 2.29 g (0.011 mole) N-benzyloxycarbonyl-O-methylisourea was dissolved (the amine not very soluble) in toluene and heated to 60° C. for three hours followed by stirring at room temperature over night. The mixture was evaporated and the 1H-NMR showed that the reaction was not completed. The mixture was therefore dissolved in 15 ml acetonitrile and heated to 60° C. for three hours followed by stirring at room temperature over night. The solvent was evaporated and the mixture was dissolved in CH2Cl2, washed once with water, dried (Na2 SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.70 g (25%) of the product.

Aufarbeitung

  1. customThe mixture was evaporated
  2. dissolutionThe mixture was therefore dissolved in 15 ml acetonitrile
  3. temperatureheated to 60° C. for three hours
  4. stirringby stirring at room temperature over night
  5. customThe solvent was evaporated
  6. dissolutionthe mixture was dissolved in CH2Cl2
  7. washwashed once with water
  8. customdried (Na2 SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-66270614c8d046a8af9a342eb13c4b24
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723444

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