Sodium Hydroxide → HCID 67406822, compound

HRID 1372616Notes

Reaction equation

HRID 1372616 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[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]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67405102HCID 67405102, compound

Product 1

HCID 67406822HCID 67406822, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)propionate (2.84 g, 9.30 mmol) was dissolved in THF (40 ml). To the resulting solution was added 0.25N NaOH (40 ml) and the mixture was stirred at room temperature for 19 hours. The solvent was distilled off under reduced pressure. After the residue was acidified with 1N HCl, extraction was conducted with ethyl acetate. The extract was washed with ice water and brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (2.48 g, 92%) was obtained as a colorless oil (this compound was provided for the subsequent reaction without further purification).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionAfter the residue was acidified with 1N HCl, extraction
  3. washThe extract was washed with ice water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent, whereby the title compound (2.48 g, 92%)
  7. customwas obtained as a colorless oil (this compound
  8. customwas provided for the subsequent reaction without further purification)

Sources & evidence

ORD record
ord-fe6d0213991c4856873edf7b7cbb9d56
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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