Acetic Anhydride → HCID 53985717, compound

HRID 1413082Notes

Reaction equation

HRID 1413082 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[C:8](OC(=O)C)(=[O:10])[CH3:9]>N1C=CC=CC=1>[C:8]([O:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11029774(3S)-3-hydroxypyrrolidin-2-one

Product 1

HCID 53985717HCID 53985717, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.439 g of (S)-(-)-3-hydroxy-2-pyrrolidinone [P. W. K. Woo, Tetrahedron Letters, 2617 (1971); mp. 103.5°-104.5° C., [α]D26 =-118.8°±2.3° (c=0.688, CHCl3)] in 14 ml of pyridine is added 2.8 ml of acetic anhydride, and the mixture is allowed to stand at room temperature for 4 hours and concentrated under reduced pressure at a temperature below 40° C. The residue is crystallized from ether and recrystallized from methylene chloride-n-hexane to give 1.735 g of (S)-(-)-3-acetoxy-2-pyrrolidinone in 86.3% yield.

Workup

  1. concentrationconcentrated under reduced pressure at a temperature below 40° C
  2. customThe residue is crystallized from ether
  3. customrecrystallized from methylene chloride-n-hexane

Sources & evidence

ORD record
ord-50edda6ea42b4d1287d33f6d716b1679
Source dataset
uspto-grants-1981_02
Patent number
US04248865

Reaction notes

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