Hydrochloric Acid → 1-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

HRID 2302115

Reaction equation

HRID 2302115 reaction equation
[H-].[Na+].C(O[C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].Cl.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C>C1COCC1.CCOCC>[CH2:22]([O:21][C:17]([CH:18]1[C:6](=[O:16])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:19]1)=[O:20])[CH3:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 24758Sodium hydrideHCID 357729Ethyl 2-((tert-butoxycarbonyl)amino)acetate

Product 1

HCID 108689421-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylateYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing suspension of 1.58 g (66 mmol) sodium hydride in 100 ml THF was added dropwise a solution of 12.79 g (60 mmol) N-tert-butyloxycarbonyl-glycine ethyl ester and 7.15 g (66 mmol) ethyl acrylate in 100 ml THF. After the addition was complete the mixture was heated to reflux for additional 2 h. The clear solution was cooled to room temperature, poured on 100 ml ether/100 ml water and acidified under vigorous stirring with 1N hydrochloric acid against methyl orange. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic layers were washed with sat. sodium bicarbonate and brine, dried over MgSO4 and evaporated. Short-path distillation of the residue gave 10.92 g (71%) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester as a colorless oil, b.p. 119-122° C. (0.2 mbar), which solidified on prolonged standing in the freezer.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureto reflux for additional 2 h
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted three times with ether
  6. washThe combined organic layers were washed with sat. sodium bicarbonate and brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. distillationShort-path distillation of the residue

Sources & evidence

ORD record
ord-de039629f2244c59bbe97ee9d1d9fe3d
Source dataset
uspto-grants-2002_08
Patent number
US06429288B1

Linked notes

Loading…