Water → 5-(Benzyloxy)-2,3-dihydro-1H-indole

HRID 2212526Notes

Reaction equation

HRID 2212526 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-]C#N.[Na+].O.[OH-].[K+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 146245-BenzyloxyindoleHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 167948815-(Benzyloxy)-2,3-dihydro-1H-indoleYield 89.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In analogy to the method described by Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859–860, the following reaction was performed. To a precooled solution of 22.3 g (0.1 mol) 5-benzyloxyindole in 270 ml acetic acid, 19 g (0.3 mol) NaCNBH3 were added. The solution was stirred at RT for 2 h, the volume was reduced to one third and poured into 300 ml water. KOH was added under cooling and the solution was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated to yield 20.1 g (89%) 5-Benzyloxy-2,3-dihydro-1H-indole as colorless oil, MS: 225 (M).

Workup

  1. customHoffmann Synthesis 1977, 859–860
  2. customthe following reaction
  3. temperatureunder cooling
  4. extractionthe solution was extracted with ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-5ad8b4954ea04fea972d9a3833a3baff
Source dataset
uspto-grants-2006_09
Patent number
US07102007B2

Reaction notes

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