Trifluoroacetic acid → (3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-one

HRID 1917553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917553
C(O[C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10](C)[C:9]1=[O:17])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:6][N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[NH:10][C:9]1=[O:17]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67437672(3aSR,6aRS)-3-Methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 59655249(3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-oneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3aSR, 6aRS)-3-methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 106, step 2) (1.99 g, 8.28 mmol) in 30 ml of dichloromethane was added trifluoroacetic acid (7.55 g, 5.1 ml, 66.3 mmol, 8 equiv.) and the yellow solution was stirred at for 5 h at room temperature. The reaction mixture was quenched by addition of saturated sodium bicarbonate solution and the pH of the aqueous phase was set to 9. After workup with dichloromethane/water, the organic phases were dried, filtered and concentrated in vaccuo to yield 1.07 g of an off-white solid, which was taken up in cold ethyl acetate and filtered to yield the title compound (822 mg, 71%) as a crystalline white solid which was directly used in the next step without further characterisation.

Aufarbeitung

  1. customThe reaction mixture was quenched by addition of saturated sodium bicarbonate solution
  2. dry with materialAfter workup with dichloromethane/water, the organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo

Quellen und Nachweise

ORD-Eintrag
ord-9d19aa9b9ca34feea3028d81dc35fa9c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618296B2

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