2-Bromothiazole → HCID 69235537, compound

HRID 1880647Notes

Reaction equation

HRID 1880647 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([O:11][C:12]([N:14]1[CH2:21][CH:20]2[CH:16]([CH2:17][NH:18][CH2:19]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(O)CCC>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH:16]2[CH:20]([CH2:19][N:18]([C:2]3[S:3][CH:4]=[CH:5][N:6]=3)[CH2:17]2)[CH2:21]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

Product 1

HCID 69235537HCID 69235537, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 541 μl (6.0 mmol) 2-bromothiazole and 1.27 g (6.0 mmol) hexahydro-pyrrolo[3,4-c]pyrrol-2-carboxylic acid tert-butyl-ester in n-butanol (10 ml) was heated for 2 h under reflux. Subsequently, the solvent was removed in vacuo and the residue taken up by chloroform. This solution was washed with water and brine in turn, dried over MgSO4, filtered and concentrated in vacuo. Column chromatography was carried out on the residue (SiO2, DCM/EtOH 10:1), yielding 450 mg (1.53 mmol, 25%) 5-thiazol-2-yl-hexahydro-pyrrolo[3,4-c]pyrrol-2-carboxylic acid tert-butyl-ester.

Workup

  1. temperatureunder reflux
  2. customSubsequently, the solvent was removed in vacuo
  3. washThis solution was washed with water and brine in turn
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5f6e74c3ec94ba4a387cc60caf5bac1
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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