2-Indanone → HCID 13132277, compound

HRID 1248053Notes

Reaction equation

HRID 1248053 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

In a solution of 10 g of indan-2-one in 200 ml of methanol is dissolved 20 g of glycine ethyl ester hydrochloride, and 5.0 g of sodium cyanoborohydride is added portionwise under ice cooling and stirring. After stirring at room temperature for 2 hours, the reaction mixture is poured into 500 ml of ice-water, make alkaline with sodium hydrogen carbonate and subjected to extraction with 300 ml of ethyl acetate. The extract is washed with water and dried, thereafter the ethyl acetate is distilled off under reduced pressure, 10 ml of 20% alcoholic 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 precipitates are collected by filtration and dried to give 11 g of N-(2-indanyl)glycine ethyl ester hydrochloride as colorless needles. Melting point: 165°-167° C.

Workup

  1. additionis added portionwise under ice cooling
  2. stirringAfter stirring at room temperature for 2 hours
  3. extractionsubjected to extraction with 300 ml of ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. distillationthe ethyl acetate is distilled off under reduced pressure, 10 ml of 20% alcoholic hydrochloric acid and 200 ml of ethyl ether
  7. additionare added to the residue
  8. customto stand at room temperature
  9. customThe resulting crystalline precipitates
  10. filtrationare collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-5da5bd66b528459b9b1a4d546a335998
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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