Sodium borohydride → HCID 10082724, compound

HRID 889027Notes

Reaction equation

HRID 889027 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[CH2:7]1)=O)C.[BH4-].[Na+]>C(O)C>[OH:3][CH2:4][CH:6]1[CH2:7][N:8]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:19])[CH3:20])=[CH:14][CH:13]=2)[C:9](=[O:11])[CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 508737211-(4-Isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 10082724HCID 10082724, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
12.5 °C

Procedure

A mixture of 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester obtained in step 2 (0.7 g, 2.65 mmol) and ethanol were cooled to 10-15° C. Sodium borohydride (0.25 g, 6.6 mmol) was added portion wise over a period of 20 min and the reaction mixture was stirred for 3.5 hrs at 20-25° C. The organic volatiles were evaporated and the residue was taken into brine solution (15 ml). The aqueous layer was extracted with ethyl acetate, dried over Na2SO4 and evaporated to obtain 4-hydroxymethyl-1-(4-isopropyl-phenyl)-pyrrolidin-2-one as an off white solid (0.5 g, 81%).

Workup

  1. customThe organic volatiles were evaporated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-cc5cabd99e92486587ed767865f30a91
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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