Potassium Carbonate → trans-2-(Benzylamino)-3,3-difluorocyclopentanol

HRID 81151Notes

Reaction equation

HRID 81151 reaction equation
C([O:4][C@@H:5]1[CH2:9][CH2:8][C:7]([F:11])([F:10])[C@H:6]1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:13]([NH:12][C@@H:6]1[C:7]([F:10])([F:11])[CH2:8][CH2:9][C@H:5]1[OH:4])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86724503HCID 86724503, compound

Product 1

HCID 86724505trans-2-(Benzylamino)-3,3-difluorocyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of trans-2-(benzylamino)-3,3-difluorocyclopentyl acetate (100 mg, 0.37 mmol) in CH3OH (2 mL), K2CO3(52 mg, 0.37 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 1 hour and concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford trans-2-(benzylamino)-3,3-difluorocyclopentanol. MS ESI calc'd. for C12H15F2NO [M+H]+ 228. found 228.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c7f5b7b8a5846cc9c2cde5af6eab1bc
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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