Lithium Chloride → 1-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

HRID 855577Notes

Reaction equation

HRID 855577 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14](OCC)=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH:10]([CH2:14][OH:15])[CH2:11][C:12]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 21935588Ethyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylate

Product 1

HCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylate (0.25 g, 1.0 mmol) in ethanol (10 ml) was added lithium chloride (0.085 g, 2.0 mmol) and sodium borohydride (0.080 g, 2.0 mmol). The reaction was stirred 24 hours at room temperature. The solvent was removed and 30 ml water was added to the residue. The aqueous solution was acidified with conc. HCl until the pH was ˜2-3. The acidic solution was extracted with EtOAc (3×75 ml). The organic layer was then washed with water (100 ml), dried with sodium sulfate and evaporated. The residue was purified using preparative TLC (15:1 DCM: MeOH) to yield 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one (H HNMR). This was repeated twice.

Workup

  1. customThe solvent was removed
  2. addition30 ml water was added to the residue
  3. extractionThe acidic solution was extracted with EtOAc (3×75 ml)
  4. washThe organic layer was then washed with water (100 ml)
  5. dry with materialdried with sodium sulfate
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-37e3dbf7eced47ae826166cccaee6efb
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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