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

HRID 1975002Notes

Reaction equation

HRID 1975002 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 3 hours at room temperature, and the aqueous phase is separated off and extracted twice using 100 ml portions of methylene chloride. The organic solutions are dried over magnesium sulphate, concentrated and distilled.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted twice
  3. dry with materialThe organic solutions are dried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-8509c70b9430404b8dd95226c359c9f5
Source dataset
uspto-grants-1994_02
Patent number
US05284855

Reaction notes

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