Ethyl Acetate → HCID 15838064, compound

HRID 2278652Notes

Reaction equation

HRID 2278652 reaction equation
C([BH3-])#N.[Na+].[C:5]1([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].C(OCC)(=O)C>FC(F)(F)C(O)=O>[C:5]1([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][CH2:14][NH:15]3)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 5003444Sodium cyanoborohydrideHCID 158062984-Phenyl-1H-indole

Product 1

HCID 15838064HCID 15838064, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
-5 °C

Procedure

1.0 g of sodium cyanoborohydride is gradually added to a solution of 1.5 g of 4-phenylindole in 20 ml of trifluoroacetic acid under argon, cooled to a temperature of about −5° C. The reaction mixture is stirred at a temperature of about 0° C. for 2 hours, and is then poured into 50 g of ice and alkalinized with 30 ml of a concentrated sodium hydroxide solution. After the addition of 100 ml of ethyl acetate, the mixture is stirred at ambient temperature and treated with 10 ml of concentrated sodium hydroxide, and then separated by settling out. The organic phase is dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is treated again with a mixture of 50 ml of water, 50 ml of ethyl acetate and 10 ml of a concentrated sodium hydroxide solution and stirred at ambient temperature for 15 minutes, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 2×50 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is triturated from 20 ml of diisopropyl ether and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 50 g column of 20-45 μm silica, elution being carried out with pure dichloromethane. 0.74 g of 4-phenyl-2,3-dihydro-1H-indole is thus obtained in the form of a cream-colored solid, the characteristics of which are the following:

Workup

  1. stirringthe mixture is stirred at ambient temperature
  2. customseparated
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. additionThe residue is treated again with a mixture of 50 ml of water, 50 ml of ethyl acetate and 10 ml of a concentrated sodium hydroxide solution
  7. stirringstirred at ambient temperature for 15 minutes
  8. customseparated
  9. customThe organic phase is separated
  10. extractionthe aqueous phase is extracted with 2×50 ml of ethyl acetate
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure
  14. customThe residue is triturated from 20 ml of diisopropyl ether
  15. concentrationconcentrated to dryness under reduced pressure
  16. customThe residue is purified by chromatography on a 50 g column of 20-45 μm silica, elution

Sources & evidence

ORD record
ord-eb8d5d1029754081a2b5a9b8a4cd4832
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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