Thiophene → methyl N-(decahydro-1-naphthalenyl)glycine

HRID 621383Notes

Reaction equation

HRID 621383 reaction equation
[C:1]1(=O)[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Cl.[CH3:13][NH:14][CH2:15][C:16]([OH:18])=[O:17].S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>CO.[Pd]>[CH3:13][N:14]([CH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1)[CH2:15][C:16]([OH:18])=[O:17]

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 98501Bicyclo[4.4.0]decan-1-oneHCID 517044Potassium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 70377605methyl N-(decahydro-1-naphthalenyl)glycineYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 64 parts of octahydro-1(2H)-naphthalenone, 50 parts of methyl glycine hydrochloride, 2 parts of a solution of thiophene in methanol 4%, 560 parts of methanol and 50 parts of potassium acetate was hydrogenated at normal pressure and at room temperature with 5 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 a mixture of water and trichloromethane. The whole was treated with a sodium hydroxide solution. The separated organic layer was dried, filtered and evaporated, yielding 82.2 parts (91.1%) of methyl N-(decahydro-1-naphthalenyl)glycine as a residue (intermediate 1).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue was taken up in a mixture of water and trichloromethane
  4. additionThe whole was treated with a sodium hydroxide solution
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7c9eacba54b14dbc9c848641b1f7f478
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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