Lithium Hydroxide → HCID 84653985, compound

HRID 1771091Notes

Reaction equation

HRID 1771091 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[C:6](=[O:9])[CH:5]([C:10]([O:12]CC)=[O:11])[CH2:4]1)[CH3:2].[Li+].[OH-].C(Cl)Cl>C1COCC1.O>[CH2:1]([N:3]1[C:7](=[O:8])[C:6](=[O:9])[CH:5]([C:10]([OH:12])=[O:11])[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 219264ethyl 1-ethyl-4,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 84653985HCID 84653985, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 1-ethyl-4,5-dioxopyrrolidine-3-carboxylate (150 mg, 0.753 mmol) and LiOH (43.3 mg, 1.81 mmol) in THF (0.5 mL) and H2O (0.5 mL) was heated at 80° C. for 1 h using microwave irradiation. The reaction solution was concentrated under reduced pressure and acidified with 1 N aqueous HCl, whereupon a precipitate formed. CH2Cl2 was added to the suspension and the precipitate was collected by filtration and dried in vacuo to provide Intermediate 8 (92.1 mg, 71.4% yield). HPLC/MS (Method D) RT=0.48 min, [M+H]+ 172.1; 1H NMR (400 MHz, Solvent) (δ ppm): 1.11-1.24 (m, 3H), 3.53 (q, J=7.28 Hz, 2H), 3.84 (s, 0.47H), 4.04 (s, 1.53H).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customformed
  4. filtrationthe precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8d083a6f10194ba6a6735a700fea174d
Source dataset
uspto-grants-2016_02
Patent number
US09249096B2

Reaction notes

Loading…