2-Tetralone → HCID 13201327, compound

HRID 1632364Notes

Reaction equation

HRID 1632364 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:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][C:19]1=O>CO>[ClH:1].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][CH:24]1[CH2:25][CH2:26][C:27]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23]1)[CH3:3]

Participants

6

Reactant 4

HCID 682662-TetraloneHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13201327HCID 13201327, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a solution of 20 g of 1,2,3,4-tetrahydro-2-naphthalenone in 200 ml of methanol, there is dissolved 23 g of glycine ethyl ester hydrochloride, and 9.0 g of sodium cyanoborohydride is added portionwise 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 500 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 crystalline precipitate is collected by filtration and dried to give 25 g of N-(1,2,3,4-tetrahydronaphthalen-2-yl)glycine ethyl ester hydrochloride as colorless needles melting at 198°-200° C.

Workup

  1. additionis added portionwise with ice cooling
  2. stirringAfter stirring at room temperature for 2 hours
  3. extractionextracted with 500 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% ethanolic hydrochloric acid and 200 ml of ethyl ether
  7. additionare added to the residue
  8. customto stand at room temperature
  9. filtrationThe crystalline precipitate is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-5326f5907a6f444c8eed52cfb8d87d61
Source dataset
uspto-grants-1984_10
Patent number
US04474692

Reaction notes

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