Sodium borohydride → 1-(4-Chlorophenyl)-3-(hydroxymethyl)pyrrolidin-2-one

HRID 1740378Notes

Reaction equation

HRID 1740378 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([C:15](OCC)=[O:16])[C:11]2=[O:20])=[CH:6][CH:5]=1.[Cl-].[Ca+2].[Cl-]>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[C:11]2=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 18544410Ethyl 1-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate

Product 1

HCID 218386441-(4-Chlorophenyl)-3-(hydroxymethyl)pyrrolidin-2-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under ice-cooling, 3.9 g of sodium borohydride was added portionwise to a solution of 30.0 g of 1-(4-chlorophenyl)-3-ethoxycarbonyl-2-pyrrolidinone and 15 g of anhydrous calcium chloride in 150 mL of methanol. After completion of the reaction, the mixture was concentrated, and water and ethyl acetate were added. The mixture was acidified with diluted hydrochloric acid. After separation, the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was crystallized with n-hexane-ethyl ether. The crystals were collected by filtration, washed with a mixture of n-hexane and diethyl ether and dried in vacuo to give 23.3 g of the title compound.

Workup

  1. temperatureUnder ice-cooling
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated
  4. additionwater and ethyl acetate were added
  5. customAfter separation
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized with n-hexane-ethyl ether
  10. filtrationThe crystals were collected by filtration
  11. washwashed with a mixture of n-hexane and diethyl ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-ff482b211dcf4abfad68e6fd86be85cd
Source dataset
uspto-grants-1999_10
Patent number
US05969138

Reaction notes

Loading…