Hydrochloric Acid → 3-Amino-3-methylpiperidine-2,6-dione hydrochloride

HRID 429221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429221
C(OC([N:11]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]([NH2:19])([CH3:18])[C:12]1=[O:20])=O)C1C=CC=CC=1.[ClH:21].[H][H].O>C(O)C.[Pd]>[ClH:21].[NH2:19][C:13]1([CH3:18])[CH2:14][CH2:15][C:16](=[O:17])[NH:11][C:12]1=[O:20]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21928242N-Benzyloxycarbonyl-alpha-amino-alpha-methylglutarimideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochlorideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

N-Benzyloxycarbonyl-α-amino-α-methylglutarimide (2.3 g, 8.3 mmol) was dissolved in ethanol (200 mL) with gentle heat and the resulting solution allowed to cool to room temperature. To this solution was added 4N hydrochloric acid (3 mL) followed by 10% Pd/C (0.4 g). The mixture was hydrogenated in a Parr apparatus under 50 psi of hydrogen for 3 hours. To the mixture was added water (50 mL) to dissolve the product. This mixture was filtered through a Celite pad which was washed with water (50 mL). The filtrate was concentrated in vacuo to afford a solid residue. The solid was slurried in ethanol (20 mL) for 30 min. The slurry was filtered to afford 1.38 g (93%) of α-amino-α-methylglutarimide hydrochloride as a white solid: 1H NMR (DMSO-d6) δ 11.25 (s, 1H), 8.92 (s, 3H), 2.84-2.51 (m, 2H), 2.35-2.09 (m, 2H), 1.53 (s, 3H); HPLC, Waters Nova-Pak C18 column, 4 micron, 1 mL/min, 240 nm, 20/80 CH3CN/0.1% H3PO4(aq), 1.03 min (94.6%).

Aufarbeitung

  1. temperaturewith gentle heat
  2. dissolutionto dissolve the product
  3. filtrationThis mixture was filtered through a Celite pad which
  4. washwas washed with water (50 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a solid residue
  7. filtrationThe slurry was filtered

Quellen und Nachweise

ORD-Eintrag
ord-722a38adbf044485ad812a9b9f985260
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316471B1

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