6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid → 6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505807Notes

Reaction equation

HRID 505807 reaction equation
[C:1]1([C:7]2[C:8]3[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:9]=3[NH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>CO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH:1]1([C:7]2[C:8]3[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:9]=3[NH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 586790836-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 586790966-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution (0.1 M) of 6-cyclohex-1-en-1-yl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in MeOH/AcOEt (2:1) was treated with 20% Pd(OH)2/C (10% wt.). The resulting suspension was stirred for 18 h under 45 psi of hydrogen then purged with nitrogen and filtered. The filtrate was concentrated to afford the title compound (98%) as a solid.

Workup

  1. customthen purged with nitrogen
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f5c7bcc51b6e4a439a896d179c06b6b8
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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