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

HRID 876473Notes

Reaction equation

HRID 876473 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-665b3fae5e7b4ef69987b0e5559e65bd
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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