Isovaleryl chloride → (R)-1-(3-methylbutanoyl)piperidine-3-carboxylic acid

HRID 332995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332995
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1.C([O-])(O)=O.[Na+].[CH3:15][CH:16]([CH3:21])[CH2:17][C:18](Cl)=[O:19]>O.C1COCC1>[CH3:15][CH:16]([CH3:21])[CH2:17][C:18]([N:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([OH:9])=[O:8])[CH2:2]1)=[O:19]

Komponenten

6

Edukt 3

HCID 66054Isovaleryl chlorideHCID 516892Sodium BicarbonateHCID 1796510(-)-Nipecotic acid

Produkt 1

HCID 42257258(R)-1-(3-methylbutanoyl)piperidine-3-carboxylic acidAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-piperidine-3-carboxylic acid (2.0 g, 15.48 mmol) in water (40 mL) and THF (20 mL) were added NaHCO3 (3.30 g, 38.70 mmol) and 3-methylbutanoyl chloride (2.8 mL, 23.2 mmol) at room temperature. The reaction was stirred overnight, concentrated under reduced pressure, diluted with water (50 mL) and extracted with EtOAc (1×). The aqueous layer was acidified with 1N HCl, extracted with EtOAc (3×) and the combined extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (2.53 g, 76%). MS 214 (MH+).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EtOAc (1×)
  4. extractionextracted with EtOAc (3×)
  5. dry with materialthe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd3d9890c8ac4734b976284c3cc1b32f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877922B2

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