Water → HCID 65041612, compound

HRID 2278666Notes

Reaction equation

HRID 2278666 reaction equation
C([BH3-])#N.[Na+].[CH:5]1([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:7][CH2:6]1.O.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[CH:5]1([CH:8]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9]2)[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 113895272-cyclopropyl-1H-indole

Product 1

HCID 65041612HCID 65041612, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

1.0 g of sodium cyanoborohydride is gradually added to a solution of 1.25 g of 2-cyclopropylindole in 80 ml of acetic acid under argon cooled to a temperature of about 15° C. The reaction mixture is stirred at a temperature of about 15° C. for 2 hours, and is then treated with 100 ml of water. It is then cooled to a temperature of about 5° C. and alkalinized by gradual addition of 140 ml of a 30% sodium hydroxide solution. The reaction mixture is diluted with 200 ml of ethyl acetate and is then stirred at ambient temperature for 15 hours. After settling out, the organic phase is separated and the aqueous phase is extracted with 3×200 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 taken up in a mixture of 60 ml of ethyl acetate, 40 ml of water and 10 ml of concentrated sodium hydroxide, and then the mixture is stirred at ambient temperature for 10 minutes. After 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. 1.2 g of (±)-2-cyclopropylindoline are thus obtained in the form of a brown oil which is used as it is.

Workup

  1. temperatureIt is then cooled to a temperature of about 5° C.
  2. stirringis then stirred at ambient temperature for 15 hours
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted with 3×200 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 taken up in a mixture of 60 ml of ethyl acetate, 40 ml of water and 10 ml of concentrated sodium hydroxide
  9. stirringthe mixture is stirred at ambient temperature for 10 minutes
  10. customthe organic phase is separated
  11. extractionthe aqueous phase is extracted with 2×50 ml of ethyl acetate
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-402d0c6851154fb7853d8012d25f0183
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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