Ethyl Acetate → HCID 76846474, compound

HRID 2278656Notes

Reaction equation

HRID 2278656 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2.[OH-].[Na+].C(OCC)(=O)C>FC(F)(F)C(O)=O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][CH2:16][NH:17]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11020512HCID 11020512, compound

Product 1

HCID 76846474HCID 76846474, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
-5 °C

Procedure

0.26 g of sodium cyanoborohydride is gradually added to a solution of 0.44 g of 4-(2-methoxyphenyl)indole in 5 ml of trifluoroacetic acid under argon, cooled to a temperature of about −5° C. The reaction mixture is stirred at a temperature of about −5° C. for 2 hours, and is then poured into 15 g of ice and alkalinized with 8 ml of a concentrated sodium hydroxide solution. After the addition of 30 ml of ethyl acetate, the mixture is stirred at ambient temperature for 1 hour, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 15 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 treated again with a mixture of 15 ml of water, 15 ml of ethyl acetate and 3 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 2×15 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 purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution being carried out with pure dichloromethane, at a flow rate of 30 ml/min. 0.14 g of 4-(2-methoxyphenyl)-2,3-dihydro-1H-indole is thus obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. stirringthe mixture is stirred at ambient temperature for 1 hour
  2. customseparated
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with 15 ml of ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. additionThe residue is treated again with a mixture of 15 ml of water, 15 ml of ethyl acetate and 3 ml of a concentrated sodium hydroxide solution
  9. stirringstirred at ambient temperature for 15 minutes
  10. customseparated
  11. customThe organic phase is separated
  12. extractionthe aqueous phase is extracted with 2×15 ml of ethyl acetate
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated to dryness under reduced pressure
  16. customThe residue is purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-8ef187c5946647c4b259b5e6e20232e9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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