Pyridine → HCID 15046664, compound

HRID 1707969Notes

Reaction equation

HRID 1707969 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].[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1.C(Cl)Cl>CN(C)C1C=CN=CC=1.CO>[C:11]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]#[CH:9])[C:3]1=[O:10])(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 15046660HCID 15046660, compound

Product 1

HCID 15046664HCID 15046664, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

A solution of 4.3 g of (S)-3-hydroxy-1-(2-propynyl)-2-pyrrolidinone, 10.6 ml of acetic anhydride, 0.6 ml of pyridine, 0.1 g of 4-(dimethylamino)pyridine and 85 ml of methylene chloride is stirred at room temperature for 18 hours. Twenty-five ml of methyl alcohol is added and the reaction stirred for 20 minutes. The mixture is washed with 1N hydrochloric acid and saturated sodium bicarbonate. The organic layer is dried, passed thorough a pad of hydrous magnesium silicate and concentrated in vacuo to give 4.9 g of the desired product as a pale yellow oil. [α]D26° =+60° (methylene chloride).

Workup

  1. washThe mixture is washed with 1N hydrochloric acid and saturated sodium bicarbonate
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad56d0a41cd1403896f72836d6e38569
Source dataset
uspto-grants-1994_10
Patent number
US05356885

Reaction notes

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