Phosphoric Acid → tert-butyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetate

HRID 2372577Notes

Reaction equation

HRID 2372577 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.P(O)(O)O.[C:15]([O:19][C:20](=[O:23])[CH2:21][NH2:22])([CH3:18])([CH3:17])[CH3:16].C([BH3-])#N.[Na+].P(=O)(O)(O)O>CO.O>[C:15]([O:19][C:20](=[O:23])[CH2:21][NH:22][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 119832-IndanoneHCID 5003444Sodium cyanoborohydrideHCID 12433730Glycine tert-butyl ester phosphite

Product 1

HCID 13132278tert-butyl 2-[(2,3-dihydro-1H-inden-2-yl)amino]acetateYield 62.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-Indanone (40 g) is dissolved in 300 ml of methanol, 78 g of glycine tert-butyl ester phosphite and 150 g of water are added, and then 23 g of sodium cyanoborohydride is added over 15 minutes with ice cooling and stirring. The resulting mixture is further stirred at room temperature for 4 hours. To the reaction mixture, 400 ml of 20% phosphoric acid is added portionwise over an hour, 200 ml of water is then added, the mixture is stirred for 30 minutes and then extracted with 4 portions (500 ml in total) of chloroform. The extract is dried over anhydrous sodium sulfate and then distilled under reduced pressure. 50 ml of ethanol and then 150 ml of water are added to the oil obtained, and the mixture is cooled. The crystalline precipitate is collected by filtration and recrystallized twice from aqueous ethanol to give 47 g of (indan-2-yl)-glycine tert-butyl ester as colorless prisms melting at 54°-55° C.

Workup

  1. stirringThe resulting mixture is further stirred at room temperature for 4 hours
  2. stirringthe mixture is stirred for 30 minutes
  3. extractionextracted with 4 portions (500 ml in total) of chloroform
  4. dry with materialThe extract is dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. addition50 ml of ethanol and then 150 ml of water are added to the oil
  7. customobtained
  8. temperaturethe mixture is cooled
  9. filtrationThe crystalline precipitate is collected by filtration
  10. customrecrystallized twice from aqueous ethanol

Sources & evidence

ORD record
ord-6bb484f13e9a4b399158be2872c4e548
Source dataset
uspto-grants-1992_03
Patent number
US05098892

Reaction notes

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