3-Amino-3-methylpiperidine-2,6-dione hydrochloride → HCID 67230396, Verbindung

HRID 448416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448416
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=O)[C:11]=1[C:19]([OH:21])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:23][C:24]1([CH3:32])[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]2[C:11]=1[C:19](=[O:21])[N:23]([C:24]1([CH3:32])[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31])[C:13]2=[O:15])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochlorideHCID 67230375HCID 67230375, Verbindung

Produkt 1

HCID 67230396HCID 67230396, VerbindungAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 3-(t-butoxycarbonylamino-methyl)-phthalic acid (3.3 g, 11.2 mmol) and 3-amino-3-methyl-piperidine-2,6-dione hydrochloride (2.0 g, 11.2 mmol) in pyridine (40 mL) was refluxed for 17 hours. The mixture was cooled and concentrated. The residue was dissolved in EtOAc (200 mL) and water (50 mL). The organic layer was washed with water (40 mL), Sat. NaHCO3 (40 mL), water (40 mL), and brine (40 mL), and dried (MgSO4). Solvent was removed, and the residue was purified by chromatography (Silica gel) to give [2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamic acid t-butyl ester (2.3 g, 51%): 1H NMR (CDCl3) δ 1.43 (s, 9H, 3(CH3)), 2.08 (s, 3H, CH3), 2.10-2.15 (m, 1H), 2.69-2.84 (m, 3H), 4.62 (d, J=6.5 Hz, 2H, CH2), 5.46 (m, 1H, NH), 7.64-7.76 (m, 3H, Ar), 8.15 (s, 1H, NH).

Aufarbeitung

  1. temperaturewas refluxed for 17 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc (200 mL)
  5. washThe organic layer was washed with water (40 mL), Sat. NaHCO3 (40 mL), water (40 mL), and brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed
  8. customthe residue was purified by chromatography (Silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-d63464dd3e5c4446a4a87557b0ed7742
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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