Cyclopropylamine → (S)-2-Cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1185433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185433
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C[C:19]2N(O)N=[N:22][C:20]=2[CH:21]=1.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C.C(=O)([O-])O.[Na+].C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:15])[NH:22][CH:20]1[CH2:21][CH2:19]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 4

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Produkt 1

HCID 68599173(S)-2-Cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 10 g of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in 953 ml of DMF, 9.2 g of HOBT, 11.5 g of EDC, 3.4 g of cyclopropylamine and 13.8 g of DIPEA was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and water and dried over MgSO4. The solvents were removed under reduced pressure and the crude product was pure enough for the next reaction step.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed under reduced pressure
  5. customthe crude product was pure enough for the next reaction step

Quellen und Nachweise

ORD-Eintrag
ord-744cd156121944e1a2f52b3d77f88894
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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