Ethyl chloroformate → 5-(1,1-Dimethylethyl) 1-ethyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

HRID 1645979Notes

Reaction equation

HRID 1645979 reaction equation
[CH:1]12[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH:5]1[CH2:4][CH2:3][NH:2]2.[OH-].[Na+].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1.O>[CH:1]12[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH:5]1[CH2:4][CH2:3][N:2]2[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 225622051,1-Dimethylethyl hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 191009335-(1,1-Dimethylethyl) 1-ethyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

13 g (61.2 mmol) of tert.-butyl 2,7-diazabicyclo[3.3.0]octane-7-carboxylate are dissolved in 100 ml of toluene, a solution of 3 g of sodium hydroxide in 20 ml of water is added and 7 g (64.5 mmol) of ethyl chloroformate are added dropwise at room temperature. The mixture is stirred for three hours at room temperature, and the aqueous phase is separated off and extracted twice with 100 ml of methylene chloride each time. The organic solutions are dried over magnesium sulphate and concentrated, and the residue is distilled.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted twice with 100 ml of methylene chloride each time
  3. dry with materialThe organic solutions are dried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-6ee1268aef934f0fa734aa4e990a69c3
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

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