Sodium Hydroxide → (S)-1-((Benzyloxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 1161935Notes

Reaction equation

HRID 1161935 reaction equation
[F:1][C:2]1([F:21])[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:17]([O:19]C)=[O:18])[CH2:3]1.[OH-].[Na+]>CO>[CH2:10]([O:9][C:7]([N:5]1[CH2:6][C:2]([F:21])([F:1])[CH2:3][C@H:4]1[C:17]([OH:19])=[O:18])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 497579381-benzyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate

Product 1

HCID 53909714(S)-1-((Benzyloxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-benzyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate in methanol was refluxed with 2N NaOH (2 eq) for 2 hours. Methanol was removed and pH adjusted to 1 with 3 N HCl obtaining a suspension which was extracted several times with ethyl acetate. Combined organics were dried over Na2SO4 and evaporated to give title product as a dark brown oil.

Workup

  1. customMethanol was removed
  2. extractionwas extracted several times with ethyl acetate
  3. dry with materialCombined organics were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d45b807b8a7247658c4404f445a8707b
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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