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

HRID 1633673

Reaction equation

HRID 1633673 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

This example was carried out in analogy to: Gordon W. Gribble, Joseph H. Hoffmann Synthesis 1977, 859-860. 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 a third and poured into 300 ml water. Potassium hydroxide 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. temperatureunder cooling
  3. extractionthe solution was extracted with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-d87fea5eadef4b14ba1f76e9e3fd3b46
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Linked notes

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