Methanol → 8-Benzyl-6-hydroxy-2,8-diazaspiro[4.5]decan-1-one

HRID 1848475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848475
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]#[N:21])([C:14](OCC)=[O:15])[C:10](=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>[Pt]=O.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:14](=[O:15])[NH:21][CH2:20][CH2:19]2)[CH:10]([OH:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 887MethanolHCID 86709485Ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate

Produkt 1

HCID 867094868-Benzyl-6-hydroxy-2,8-diazaspiro[4.5]decan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a flask charged with ethyl 1-benzyl-4-(cyanomethyl)-3-oxopiperidine-4-carboxylate (900 mg, 3.0 mmol) and a stir bar was added platinum oxide (100 mg, 0.44 mmol), MeOH (20 mL) and acetic acid (20 mL). The mixture was allowed to stir vigorously under an atmosphere of hydrogen for 24 hours. LC indicated complete reaction at that point. The catalyst was removed by filtration through a pad of CELITE®, and the filtrate was concentrated under reduced pressure. The residue was dissolved in EtOH (100 mL), and K2CO3 was added (2.1 g, 15 mmol). The mixture was heated to 90° C. for 4 hours. The reaction was cooled, and DCM was added (200 mL) to precipitate the solids. The solids were then removed by filtration, and the crude reaction was adsorbed onto silica gel, and flushed out with DCM and 10% MeOH (mixed with 10% NH4OH) to give the title compound. LCMS: m/z 261 (M+H)+.

Aufarbeitung

  1. customreaction at that point
  2. customThe catalyst was removed by filtration through a pad of CELITE®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOH (100 mL)
  5. additionK2CO3 was added (2.1 g, 15 mmol)
  6. temperatureThe reaction was cooled
  7. additionDCM was added (200 mL)
  8. customto precipitate the solids
  9. customThe solids were then removed by filtration
  10. customthe crude reaction
  11. customflushed out with DCM and 10% MeOH (mixed with 10% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-4ffe3c5f74284a76ae3b4e01c3f6f809
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952166B2

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