Glycine → HCID 23712912, compound

HRID 1164669Notes

Reaction equation

HRID 1164669 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+:7].[C:8]1(=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1>CO.[Pd]>[Na+:7].[CH:8]1([NH:1][CH2:2][C:3]([O-:5])=[O:4])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 750GlycineHCID 67351-IndanoneHCID 14798Sodium Hydroxide

Product 1

HCID 23712912HCID 23712912, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Glycine (5.1 g, 0.068 mole) was dissolved in a solution of NaOH (2.72 g, 0.068 mole) and methanol (125 ml). To this was added 1-indanone (10.0 g, 0.076 mole, 10% excess) and 5% Pd/C dry (2.0 g). This mixture was subjected to hydrogen at room temperature on a Parr shaker for 24 hours. The catalyst was removed by filtration and fresh 5% Pd/C dry (2.0 g) added. Hydrogenation was resumed for 20 hours. A total of 55 psi of H2 (68 psi theory) was taken up. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure to an oily residue. This residue was dissolved in H2O (100 ml) and extracted with ethyl acetate (3×25 ml). The aqueous solution was cooled on an ice bath and a white solid precipitated. This solid was collected and air dried to give 5.0 g of crude product. A second crop was obtained by concentrating the filtrate under reduced pressure to a solid residue. This residue was recrystallized from 70% isopropanol/H2O (40 ml), collected and air dried to give 4.3 g of product. The two crops were combined, triturated in 80% isopropanol/H2O (50 ml), collected, air dried and dried in vacuo at 60° to give 6.8 g (0.037 mole, 47% yield), melting point 196°-200° (dec.).

Workup

  1. customdry (2.0 g)
  2. customThe catalyst was removed by filtration and fresh 5% Pd/C
  3. customdry (2.0 g)
  4. additionadded
  5. waitHydrogenation was resumed for 20 hours
  6. customThe catalyst was removed by filtration
  7. concentrationthe filtrate concentrated under reduced pressure to an oily residue
  8. dissolutionThis residue was dissolved in H2O (100 ml)
  9. extractionextracted with ethyl acetate (3×25 ml)
  10. temperatureThe aqueous solution was cooled on an ice bath
  11. customa white solid precipitated
  12. customThis solid was collected
  13. customair dried
  14. customto give 5.0 g of crude product
  15. customA second crop was obtained
  16. concentrationby concentrating the filtrate under reduced pressure to a solid residue
  17. customThis residue was recrystallized from 70% isopropanol/H2O (40 ml)
  18. customcollected
  19. customair dried

Sources & evidence

ORD record
ord-e087ee9e9050410cb3145d01652dcfed
Source dataset
uspto-grants-1983_01
Patent number
US04370494

Reaction notes

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