1-Benzyloxycarbonyl-3-piperidone → Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate

HRID 69923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69923
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[CH3:18][Mg+].[Br-]>C1COCC1>[OH:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

Komponenten

4

Edukt 2

HCID 15141691-Benzyloxycarbonyl-3-piperidoneHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 10634355Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of benzyl 3-oxopiperidine-1-carboxylate (2.33 g, 10 mmol) in dry THF (50 mL) at −78° C. was added MeMgBr (3.6 mL, 3M solution in THF, 11 mmol) slowly. The reaction was allowed to stir at −78° C. for 10 min then slowly warmed to r.t. The reaction was quenched with NH4Cl and dissolved in EtOAc (300 mL) and washed with saturated NH4Cl and brine, dried and filtered, and concentrated to give the crude. The crude material was further purified by silica gel chromatography to yield benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate. (53% yield). LCMS (m/z): 250.1 (MH+); LC Rt=2.98 min.

Aufarbeitung

  1. temperaturethen slowly warmed to r.t
  2. customThe reaction was quenched with NH4Cl
  3. dissolutiondissolved in EtOAc (300 mL)
  4. washwashed with saturated NH4Cl and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude
  9. customThe crude material was further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2e57a71f02f14ccc9ead6aee6a9c6ddc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822497B2

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