p-Toluenesulfonic acid → Ethyl 2,7-diazabicyclo[3.3.0]octane-2-carboxylate

HRID 1975003Notes

Reaction equation

HRID 1975003 reaction equation
[CH:1]12[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH:5]1[CH2:4][CH2:3][N:2]2[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH:1]12[CH2:8][NH:7][CH2:6][CH:5]1[CH2:4][CH2:3][N:2]2[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 191009335-(1,1-Dimethylethyl) 1-ethyl hexahydropyrrolo[3,4-b]pyrrole-1,5-dicarboxylate

Product 1

HCID 15070028Ethyl 2,7-diazabicyclo[3.3.0]octane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15.2 g (53.5 mmol) of 2-ethyl 7-tert.-butyl 2,7-diazabicyclo[3.3.0]octane-2,7-dicarboxylate in 100 ml of chloroform are refluxed for 5 hours together with 10.5 g (55.3 mol) of para-toluenesulphonic acid. The mixture is washed with 50 ml of 10% strength sodium hydroxide solution, and the organic phase is dried over potassium carbonate, concentrated and distilled.

Workup

  1. washThe mixture is washed with 50 ml of 10% strength sodium hydroxide solution
  2. dry with materialthe organic phase is dried over potassium carbonate
  3. concentrationconcentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-364eeb6b71e5406a98eb71c38ae5915f
Source dataset
uspto-grants-1994_02
Patent number
US05284855

Reaction notes

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