Thiophene → HCID 70360094, compound

HRID 1650996Notes

Reaction equation

HRID 1650996 reaction equation
[CH2:1]1[CH:14]2[CH:5]([C:6]3[C:11]([C:12](=O)[CH2:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1.Cl.[CH3:17][NH:18][CH2:19][C:20]([OH:22])=[O:21].S1C=CC=C1.[F-].[K+].[H][H]>CO.[Pd]>[CH3:17][N:18]([CH:12]1[CH2:13][CH:14]2[CH:5]([CH2:4][CH2:3][CH2:2][CH2:1]2)[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:19][C:20]([OH:22])=[O:21]

Participants

8

Reactant 5

HCID 8030ThiopheneHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 2903582,3,4,4a,10,10a-Hexahydrophenanthren-9(1H)-oneHCID 522689Potassium FluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 70360094HCID 70360094, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 46.4 parts of 2,3,4,4a,10,10a-hexahydro-9(1H)phenanthrenone, 58 parts of methyl glycine monohydrochloride, 2 parts of a solution of thiophene in methanol 4%, 480 parts of methanol and 26.1 parts of potassium fluoride was hydrogenated at normal pressure and at 50° C. with 3.0 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 1,1'-oxybisethane. The whole was treated with a sodium hydroxide solution. The separated organic layer was dried, filtered and evaporated, yielding 59.5 parts (93.8%) of methyl N-(1,2,3,4,4a,9,10,10a-octahydro-9-phenanthrenyl)glycine as a residue (int. 6).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe whole was treated with a sodium hydroxide solution
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5c1baf4c19714ba790ec4ebc584c831a
Source dataset
uspto-grants-1990_05
Patent number
US04927449

Reaction notes

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