Sodium Hydroxide → {(3S,5R)-1-[4-(trifluoromethyl)benzyl]-5-[4-(trifluoromethyl)phenyl]pyrrolidin-3-yl}acetic acid

HRID 1869767Notes

Reaction equation

HRID 1869767 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:7]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH2:6]1.[OH-].[Na+]>CO>[F:29][C:27]([F:28])([F:30])[C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:7]2[C@@H:8]([C:10]3[CH:11]=[CH:12][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:14][CH:15]=3)[CH2:9][C@@H:5]([CH2:4][C:3]([OH:31])=[O:2])[CH2:6]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76697410Methyl{1-[4-(trifluoromethyl)benzyl]-5-[4-(trifluoromethyl)phenyl]pyrrolidin-3-yl}acetate

Product 1

HCID 53630255{(3S,5R)-1-[4-(trifluoromethyl)benzyl]-5-[4-(trifluoromethyl)phenyl]pyrrolidin-3-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The ester from Step 5 (240 mg, 0.53 mmol) was dissolved in methanol (2 mL) and NaOH (0.67 mL, 2.65 mmol) was added. The mixture was heated at 60° C. for 2 h. then cooled, evaporated, neutralised with HCl (aq.) and extracted into CH2Cl2. The organic extracts were pooled, washed with water, brine and dried (MgSO4) and evaporated. The residue was purified on silica using 10-100% ethyl acetate in iso-hexane as eluant.

Workup

  1. temperaturethen cooled
  2. customevaporated
  3. extractionextracted into CH2Cl2
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on silica using 10-100% ethyl acetate in iso-hexane as eluant

Sources & evidence

ORD record
ord-bef72b08665044a6b9e774b3a37ef318
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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