2-Indanone → ethyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetate

HRID 373763Notes

Reaction equation

HRID 373763 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.Cl.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[CH3:13].C([BH3-])#N.[Na+]>C(O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:17][CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:18]

Participants

5

Reactant 3

HCID 119832-IndanoneHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13132276ethyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetateYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Indanone (25.1 g. 0.19 mol) and glycine ethyl ester hydrochloride (34.5 g, 0.247 mol) were dissolved in absolute ethanol (700 mL) and sodium cyanoborohydride (25.8 g, 0.41 mol) was added in portions to the solution. After addition the mixture was allowed to sit at room temperature overnight. The ethanol was removed under reduced pressure and the residue treated with water and extracted into ethyl acetate. The organic extract was repeatedly washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride before being dried over magnesium sulfate and filtered. After the solvent was concentrated under vacuum an oil remained which was taken up in ether/ethanol (250/50 mL) and cooled by mean of an ice-water bath. Ether which had previously been saturated with anhydrous hydrogen chloride was slowly added to the solution. The precipitated product was filtered and washed with cold ether/ethanol to yield a white solid (21 g) melting at 166°-168° C.

Workup

  1. additionAfter addition the mixture
  2. customThe ethanol was removed under reduced pressure
  3. additionthe residue treated with water
  4. extractionextracted into ethyl acetate
  5. extractionThe organic extract
  6. washwas repeatedly washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride
  7. dry with materialbefore being dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationAfter the solvent was concentrated under vacuum an oil
  10. temperaturecooled by mean of an ice-water bath
  11. additionwas slowly added to the solution
  12. filtrationThe precipitated product was filtered
  13. washwashed with cold ether/ethanol

Sources & evidence

ORD record
ord-95d66c0d8ae942bb9c5f1762da15cb56
Source dataset
uspto-grants-1992_11
Patent number
US05166154

Reaction notes

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