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

HRID 451558Notes

Reaction equation

HRID 451558 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

A solution of ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate (4.272 g, 14.4 mmol) dissolved in 3 N HCl (175 mL) was heated at reflux for 14 hours. The reaction mixture was cooled to room temperature, then solid NaHCO3 was added until pH 8 and extracted three times with ethyl acetate, the combined organic layers were dried over Na2SO4 and the solvents were evaporated. The title compound was obtained as white solid (3.5 g, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 14 hours
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-dab1da1d31fb4a0ca2b2f2cda9c71ec4
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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