Pyridine → HCID 15046664, compound

HRID 2107970Notes

Reaction equation

HRID 2107970 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10].N1C=CC=CC=1.CN(C1C=CC=CN=1)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:26]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10])(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 15046660HCID 15046660, compound

Product 1

HCID 15046664HCID 15046664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.0 g of (S)-3-hydroxy-1-(2-propynyl)-2-pyrrolidinone, 6.7 ml of pyridine, 0.2 g of dimethylaminopyridine and 6.7 ml of acetic anhydride was stirred in a water bath for 3 hours. The mixture was diluted with 150 ml of dichloromethane, washed in succession with water, sodium bicarbonate solution, 1N hydrochloric acid, sodium bicarbonate solution and brine, dried and concentrated, giving 6.4 g of (S)-3-(acetyloxy)-1-(2-propynyl)-2-pyrrolidinone [α]D260 =-45° (dichloromethane).

Workup

  1. washwashed in succession with water, sodium bicarbonate solution, 1N hydrochloric acid, sodium bicarbonate solution and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4dc6d5cef7994f3293341d1d935b441e
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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