Sodium Bicarbonate → 1-Benzyl-3,3-difluoropiperidine-4,4-diol

HRID 876473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876473
[CH2:1]([N:8]1[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[CH:10](C(OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:23].[Na+]>Cl>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([OH:16])([OH:23])[C:12]([F:14])([F:15])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 49761228Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate

Produkt 1

HCID 574158661-Benzyl-3,3-difluoropiperidine-4,4-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate (6.00 g, 20.2 mmol; prepared as described in WO 2005/040120, p. 30) was dissolved in 3N HCl (60 mL) and heated to reflux for 16 hours. The reaction was cooled, adjusted to pH 8 with solid NaHCO3, then extracted three times with ethyl acetate. The combined organics were washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to a white solid (5.1 g). MS APCI (+) m/z 244.0 (M+1) detected.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organics were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to a white solid (5.1 g)

Quellen und Nachweise

ORD-Eintrag
ord-665b3fae5e7b4ef69987b0e5559e65bd
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987251B2

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