2-Indanone → HCID 13132277, compound

HRID 1632354Notes

Reaction equation

HRID 1632354 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].[CH2:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][C:19]1=O>CO>[ClH:1].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][CH:19]1[CH2:18][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)[CH3:3]

Participants

6

Reactant 4

HCID 119832-IndanoneHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13132277HCID 13132277, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Glycine ethyl ester hydrochloride (20 g) is dissolved in a solution of 10 g of 2-indanone in 200 ml of methanol, and then 5.0 g of sodium cyanoborohydride is added portionwise to the solution with ice cooling and stirring. After stirring at room temperature for 2 hours, the reaction mixture is poured into 500 ml of ice water, and the whole mixture is made alkaline with sodium hydrogen carbonate and extracted with 300 ml of ethyl acetate. The extract is washed with water and dried, the ethyl acetate is distilled off under reduced pressure, 10 ml of 20% ethanolic hydrochloric acid and 200 ml of ethyl ether are added to the residue, and the mixture is allowed to stand at room temperature. The resulting crystalline precipitate is collected by filtration and dried to give 11 g of N-(indan-2-yl)glycine ethyl ester hydrochloride as colorless needles melting at 164°-167° C.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. extractionextracted with 300 ml of ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. distillationthe ethyl acetate is distilled off under reduced pressure, 10 ml of 20% ethanolic hydrochloric acid and 200 ml of ethyl ether
  6. additionare added to the residue
  7. customto stand at room temperature
  8. filtrationThe resulting crystalline precipitate is collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-c917abe8d3864191a44fea02fd7f8e73
Source dataset
uspto-grants-1984_10
Patent number
US04474692

Reaction notes

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