Sodium Hydroxide → (2S,4S)-1-(Tert-butoxycarbonyl)-4-(2-naphthyloxy)-2-pyrrolidinecarboxylic acid

HRID 1372580Notes

Reaction equation

HRID 1372580 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[C:24]([O:26]C)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67406330(2S,4S)-1-tert-Butyl 2-methyl 4-(naphthalen-2-yloxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 2756011(2S,4S)-1-(Tert-butoxycarbonyl)-4-(2-naphthyloxy)-2-pyrrolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylcarboxylate (5.37 g) in THF (116 ml) was added 0.25N NaOH (116 ml, 29.0 mmol). The resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was acidified with 1N HCl, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue thus obtained was recrystallized from hexane-chloroform, whereby the title compound (4.44 g, 85% (2 steps)) was obtained as white crystalline powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionfollowed by extraction with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue thus obtained
  8. customwas recrystallized from hexane-chloroform, whereby the title compound (4.44 g, 85% (2 steps))
  9. customwas obtained as white crystalline powder

Sources & evidence

ORD record
ord-87dc31d07a1c44ea83f003fb2359fcc8
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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