Triethylamine → (S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

HRID 1185428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185428
[Br:1][CH2:2][C:3](Br)=[O:4].Cl.[CH:7]1([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH2:9][CH2:8]1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:7]1([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:3](=[O:4])[CH2:2][Br:1])=[O:12])[CH2:9][CH2:8]1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 66855012(S)-N-cyclopropylpyrrolidine-2-carboxamide hydrochloride

Produkt 1

HCID 68600753(S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.2 g of bromo-acetyl bromide in 30 ml of DCM a solution of 1 g of (S)-Pyrrolidine-2-carboxylic acid cyclopropylamide hydrochloride, 0.6 g of triethylamine and 7 mg of DMAP in 10 ml of DCM was added drop-wise at 0° C. After 1 h the reaction mixture was diluted with ethyl acetate and the solids were filtered off. The organic phase was evaporated under reduced pressure and the residue was filtered over silica gel eluting with ethyl acetate/heptane (8/2). After evaporation of the solvent the obtained product was pure enough for the subsequent reaction step. Yield: 1.3 g.

Aufarbeitung

  1. filtrationthe solids were filtered off
  2. customThe organic phase was evaporated under reduced pressure
  3. filtrationthe residue was filtered over silica gel eluting with ethyl acetate/heptane (8/2)
  4. customAfter evaporation of the solvent the obtained product
  5. customwas pure enough for the subsequent reaction step

Quellen und Nachweise

ORD-Eintrag
ord-2798415fcf58488d94236db9eeabf200
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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