Glycine, N-methyl-, hydrochloride (1:1) → methyl N-(1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-yl)glycine

HRID 1650993Notes

Reaction equation

HRID 1650993 reaction equation
[CH2:1]1[CH:13]2[CH:5]([C:6]3[C:11]([C:12]2=O)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][CH2:2]1.Cl.[CH3:16][NH:17][CH2:18][C:19]([OH:21])=[O:20].C([O-])(=O)C.[Na+].[H][H]>[Pd].CO>[CH3:16][N:17]([CH:12]1[CH:13]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)[CH2:18][C:19]([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 6041812,3,4,4a-Tetrahydro-1H-fluoren-9(9aH)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 70360266methyl N-(1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-yl)glycineYield 24.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 48 parts of 1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-one, 65 parts of methyl glycine hydrochloride, 65 parts of sodium acetate and 560 parts of methanol 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 acidified with a hydrochloric acid solution. The separated aqueous layer was made alkaline and the product was extracted with trichloromethane. The combined organic layers were dried, filtered and evaporated, yielding 16.6 parts (24.8% of methyl N-(1,2,3,4,4a,9a-hexahydro-9H-fluoren-9-yl) glycine as a residue (int. 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. extractionthe product was extracted with trichloromethane
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-80d53bcc47a9480f93f5097feea753ae
Source dataset
uspto-grants-1990_05
Patent number
US04927449

Reaction notes

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