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

HRID 271236Notes

Reaction equation

HRID 271236 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 was acidified with conc. HCl until the pH was ˜2-3. The acidic solution was extracted 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
  4. extractionThe acidic solution was extracted sodium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-f843d0b7faff490c955338a32f24fd07
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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