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

HRID 1588235Notes

Reaction equation

HRID 1588235 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 stir at room temperature over night. 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 stripped under vacuum an oil remained which was taken up in ether/ethanol (250/50 mL) and cooled by means of an ice-water bath. Ether previously saturated with anhydrous hydrogen chloride was slowly added to the solution. The precipitated product was filtered off 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. temperaturecooled by means of an ice-water bath
  10. additionEther previously saturated with anhydrous hydrogen chloride was slowly added to the solution
  11. filtrationThe precipitated product was filtered off
  12. washwashed with cold ether/ethanol

Sources & evidence

ORD record
ord-745575ee0dc6457faaeb7c8a8cd4609e
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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