Sulfuric Acid → 4-(Hydroxymethyl)-1-methylpyrrolidin-2-one

HRID 1834808Notes

Reaction equation

HRID 1834808 reaction equation
[Li+].[BH4-].[C:3]([CH:7]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[CH2:8]1)(OC)=[O:4].S(=O)(=O)(O)O>C(OCC)C>[OH:4][CH2:3][CH:7]1[CH2:11][N:10]([CH3:12])[C:9](=[O:13])[CH2:8]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 108402Methyl 1-methyl-5-oxopyrrolidine-3-carboxylateHCID 4148881Lithium borohydride

Product 1

HCID 219142634-(Hydroxymethyl)-1-methylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.3g (106 m moles) of LiBH4 in 150 ml of diethyl ether was slowly added dropwise at +5° C to 17.0g (107 m mols) of 4-carbomethoxy-1-methyl-pyrrolidone in 20 ml of absolute diethyl ether. Stirring was continued for 2 hours at room temperature, then the mixture was acidified with 2N sulfuric acid (pH 2), the solvent and water were distilled off to a large extent in vacuo and the remaining residue was extracted with methylene chloride. The dried methylene chloride phase was concentrated and the residue was distilled in vacuo. 5 g of the compounds desired were obtained in a 98 % purity: nD20 : 1.4950.

Workup

  1. distillationthe solvent and water were distilled off to a large extent in vacuo
  2. extractionthe remaining residue was extracted with methylene chloride
  3. concentrationThe dried methylene chloride phase was concentrated
  4. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-4332e064dc1744829d6ee52788002db0
Source dataset
uspto-grants-1978_01
Patent number
US04071530

Reaction notes

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