4-Amino-1-Boc-piperidine → HCID 23401055, Verbindung

HRID 488932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488932
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>CN(C=O)C>[C:25]([O:24][C:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10](=[O:11])[NH2:12])=[CH:8][CH:7]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Komponenten

4

Edukt 2

HCID 12682914-Amino-1-Boc-piperidineHCID 122382474-(2,3-Epoxypropoxy)benzamide

Produkt 1

HCID 23401055HCID 23401055, VerbindungAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Oxiranylmethoxy-benzamide (76 mg, 0.393 mmol) was dissolved in 8 mL of dry DMF, followed by the addition of 4-amino-1-N-boc-piperidine (178 mg, 0.889 mmol). The reaction mixture was stirred at 80° C. for 48 h. The reaction mixture was concentrated and the residue was purified by flash chromatography eluting with 0-5% 2M NH3 in MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 62 mg of 4-[3-(4-carbamoyl-phenoxy)-2-hydroxy-propylamino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluting with 0-5% 2M NH3 in MeOH/CH2Cl2
  4. customThe product fractions were collected
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6142fcd4ff804c8588f941d646def2ab
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974870B2

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