Water → HCID 20766264, compound

HRID 2278604Notes

Reaction equation

HRID 2278604 reaction equation
C([BH3-])#N.[Na+].[CH:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH3:7])[CH3:6].O.[OH-].[Na+]>C(O)(=O)C>[CH:5]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 873072-Isopropyl-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20766264HCID 20766264, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

4.65 g of sodium cyanoborohydride are gradually added to a solution of 5.0 g of 2-isopropylindole in 50 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 25 ml of water. It is then cooled to a temperature of about 5° C. and alkalinized by gradual addition of powdered sodium hydroxide. The reaction mixture is allowed to warm up to ambient temperature and is then stirred for 16 hours. The precipitate is filtered off through sintered glass and washed with 50 ml of water and then 50 ml of ethyl acetate. The filtrate is diluted with 50 ml of water and 70 ml of ethyl acetate and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 2×100 ml of ethyl acetate. The organic phases are combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 90 g cartridge of 15-40 μm silica, elution being carried out with a 95/5 v/v cyclohexane/ethyl acetate mixture, at a flow rate of 50 ml/min. 4.0 g of (±)-2-isopropylindoline are thus obtained in the form of a colorless oil which crystallizes into a white solid, the characteristics of which are the following:

Workup

  1. temperatureIt is then cooled to a temperature of about 5° C.
  2. temperatureto warm up to ambient temperature
  3. stirringis then stirred for 16 hours
  4. filtrationThe precipitate is filtered off through sintered glass
  5. washwashed with 50 ml of water
  6. additionThe filtrate is diluted with 50 ml of water and 70 ml of ethyl acetate
  7. customseparated
  8. customThe organic phase is separated
  9. extractionthe aqueous phase is extracted with 2×100 ml of ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure
  14. customThe residue is purified by chromatography on a 90 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-d303e778e1f9411183708911a6db064a
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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