Potassium Carbonate → trans-N-benzyl-2-chloro-N-(2,2-difluoro-5-hydroxycyclopentyl)acetamide

HRID 81152Notes

Reaction equation

HRID 81152 reaction equation
ClCC([O:5][C@@H:6]1[CH2:10][CH2:9][C:8]([F:12])([F:11])[C@H:7]1[N:13]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14](=[O:17])[CH2:15][Cl:16])=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:18]([N:13]([C@H:7]1[C@H:6]([OH:5])[CH2:10][CH2:9][C:8]1([F:11])[F:12])[C:14](=[O:17])[CH2:15][Cl:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86724507trans-2-(N-benzyl-2-chloroacetamido)-3,3-difluorocyclopentyl 2-chloroacetate

Product 1

HCID 86724506trans-N-benzyl-2-chloro-N-(2,2-difluoro-5-hydroxycyclopentyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of trans-2-(N-benzyl-2-chloroacetamido)-3,3-difluorocyclopentyl 2-chloroacetate (480 mg, 1.26 mmol) in CH3OH (15 mL), K2CO3 (175 mg, 1.26 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 3 hours and then concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford trans-N-benzyl-2-chloro-N-(2,2-difluoro-5-hydroxycyclopentyl)acetamide. MS ESI calc'd. for C14H16ClF2NO2 [M+H]+ 304. found 304.

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-95293b78191f497a91bbae6a85317f2a
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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