Thiophene → HCID 70360090, compound

HRID 1762042Notes

Reaction equation

HRID 1762042 reaction equation
[CH2:1]1[CH:5]2[C:6](=O)[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH:4]2[CH2:3][CH2:2]1.Cl.[CH3:15][NH:16][CH2:17][C:18]([OH:20])=[O:19].S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>CO.[Pd]>[CH3:15][N:16]([CH:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[CH:4]2[CH2:3][CH2:2][CH2:1][CH:5]12)[CH2:17][C:18]([OH:20])=[O:19]

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 316916Cyclopent[a]inden-8(1H)-one, 2,3,3a,8a-tetrahydro-HCID 517044Potassium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 70360090HCID 70360090, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 23.4 parts of 2,3,3a,8a-tetrahydrocyclopent[a]inden8(1H)-one, 31.4 parts of methyl glycine hydrochloride, 1 part of a solution of thiophene in methanol 4%, 400 parts of methanol and 13.3 parts of potassium acetate was hydrogenated at normal pressure and at room temperature with 2.0 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and the product was extracted with dichloromethane. The extract was washed with a hydrochloric acid solution and a sodium hydroxide solution, dried, filtered and evaporated, yielding 29.0 parts (86.9%) of methyl N-(1,2,3,3a,8,8a-hexahydrocyclopent[a]inden-8-yl)-glycine as a residue (int. 3).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionthe product was extracted with dichloromethane
  4. washThe extract was washed with a hydrochloric acid solution
  5. dry with materiala sodium hydroxide solution, dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a73ef35d8ab7412fb5316d228f2ed943
Source dataset
uspto-grants-1989_05
Patent number
US04830664

Reaction notes

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