Tetrahydrofuran → 1-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

HRID 2194837Notes

Reaction equation

HRID 2194837 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](OC)=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].C1COCC1>CO>[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 8028TetrahydrofuranHCID 2969493Methyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 mL round-bottomed flask was charged with methyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylate 52 (7.50 g, 31.6 mmol), sodium borohydride (1.32 g, 34.8 mmol), and 100 mL of THF. After being heated to reflux, 15 mL of MeOH was slowly added. After 1 h at reflux, the reaction was concentrated, 100 mL of water was added, and the mixture was extracted with DCM. The combined extracts were dried and concentrated to give 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one 53.

Workup

  1. temperatureAfter being heated
  2. temperatureto reflux
  3. temperatureAfter 1 h at reflux
  4. concentrationthe reaction was concentrated
  5. addition100 mL of water was added
  6. extractionthe mixture was extracted with DCM
  7. customThe combined extracts were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-04ad25007de045b3a5ebda4da637cc98
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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