Acetic Anhydride → 3-(Acetyloxy)-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

HRID 1534541Notes

Reaction equation

HRID 1534541 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[C:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]1=[O:16].[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[C:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:3]1=[O:16])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15046675(S)-3-hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Product 1

HCID 199098783-(Acetyloxy)-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.4 of (S)-3-hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone and 1.0 ml of acetic anhydride in 20 ml of dichloromethane was stirred overnight. The solvent was removed in vacuo. The residue was basified with potassium bicarbonate solution and extracted with dichloromethane. The dichloromethane solution was washed with water, dried, concentrated in vacuo and the residue was purified by chromatography (alumina), giving the desired product.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane solution was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-2623ee8484bd4977b15ce6056a9789c9
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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