Skatole → 3-Methylindoline

HRID 1640260Notes

Reaction equation

HRID 1640260 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[OH-].[Na+]>C(O)(=O)C>[CH3:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH2:7]1

Participants

5

Reactant 3

HCID 6736SkatoleHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 5245043-Methylindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere 0.58 g (9.2 mmol) sodium cyanoborohydride were added batchwise to 1.0 g (7.6 mmol) 3-methylindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed several times with saturated sodium hydrogen carbonate solution
  3. customdried on sodium sulphate
  4. customevaporated down

Sources & evidence

ORD record
ord-e31a142316a845c796dfb9f835fb59be
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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