Ethyl 1H-indole-3-acetate → Ethyl (2,3-dihydro-1H-indol-3-yl)acetate

HRID 1174526Notes

Reaction equation

HRID 1174526 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.C([BH3-])#N.[Na+]>C(O)(=O)C.[OH-].[Na+].ClCCl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH2:2]1)[CH3:15]

Participants

6

Reactant 2

HCID 13067Ethyl 1H-indole-3-acetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21795444Ethyl (2,3-dihydro-1H-indol-3-yl)acetateYield 78.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl indole-3-acetate (4 g, 19 mmol, 98%) was taken up in acetic acid (40 cm3) and sodium cyanoborohydride (4 g, 63 mmol) was added. The reaction was stirred at room temperature for 2 h, then diluted with aqueous sodium hydroxide until basic. The aqueous mixture was extracted with ethyl acetate and the organic layer was separated, dried and concentrated to dryness under reduced pressure. The solid obtained was taken up in dichloromethane and chromatographed on silica eluting with dichloro-methane with increasing volumes of methanol. The product containing fractions were combined and concentrated to yield ethyl-2,3-dihydro-indole-3-acetate as a solid (3 g, 15 mmol, 78%).

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe solid obtained
  6. customchromatographed on silica eluting with dichloro-methane with increasing volumes of methanol
  7. additionThe product containing fractions
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b1af29fb948e4562a68bb36c89d0be54
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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