Sodium Hydroxide → 1H-Indole, 2,3-dihydro-5-(1-methylethyl)-

HRID 356019Notes

Reaction equation

HRID 356019 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)[CH3:3].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 105589185-(Propan-2-yl)-1H-indole

Product 1

HCID 106785501H-Indole, 2,3-dihydro-5-(1-methylethyl)-Yield 102.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a cooled solution of indole (D17, 0.60 g, 3.75 mmol) in glacial acetic acid (12 ml) was added sodium cyanoborohydride (1.20 g, 19.1 mmol) in portions. The mixture was stirred under argon for 4 h, then diluted with water and basified with 10% aqueous sodium hydroxide. The mixture was extracted with dichloromethane and the extract was dried and evaporated. After combining with material from a previous experiment (from 0.14 g indole) the crude product was chromatographed on silica gel eluted with diethyl ether to give the title compound (0.62 g, 84%).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe extract was dried
  3. customevaporated
  4. customwas chromatographed on silica gel
  5. washeluted with diethyl ether

Sources & evidence

ORD record
ord-ca5e348a5a57460995cf8e5ac5d5fc50
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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