1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl cis(+/-)-3-(benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidine-1-carboxylate

HRID 1425029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425029
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[C:28](O)=[O:29].CCN=C=NCCCN(C)C>CC(N(C)C)=O.CN(C1C=CN=CC=1)C.ClCCl>[CH2:16]([O:15][C@H:3]1[C@@H:2]([NH:1][C:28]([C:24]2[NH:23][CH:27]=[CH:26][N:25]=2)=[O:29])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5743211H-Imidazole-2-carboxylic acidHCID 86648571tert-Butyl cis(+/-)-4-amino-3-(benzyloxy)piperidine-1-carboxylate

Produkt 1

HCID 86648572tert-Butyl cis(+/-)-3-(benzyloxy)-4-[(1H-imidazol-2-ylcarbonyl)amino]piperidine-1-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

tert-Butyl cis(±)-4-amino-3-(benzyloxy)piperidine-1-carboxylate obtained in Example (90d) (0.92 g, 3.0 mmol) was dissolved in DMA (10 mL). 1H-Imidazol-2-ylcarboxylic acid (0.19 g, 1.70 mmol), WSC (0.82 g, 0.43 mmol) and DMAP (60 mg, 0.49 mmol) were added, and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with dichloromethane, washed with water and brine, and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1, 1/1, 1/3) to obtain 0.31 g of the title compound as a colorless solid (46%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1, 1/1, 1/3)

Quellen und Nachweise

ORD-Eintrag
ord-3d29af1a529d476e8d6e7369e2979b26
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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