Red-Al → 4-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile

HRID 268793Notes

Reaction equation

HRID 268793 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[OH:3][CH2:4][CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 673560383-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 673762644-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester LIX (648 mg, 2.04 mmol) in THF (20 ml) was added Red-Al (65% w, 1.96 ml, 6.87 mmol) dropwise. The mixture was stirred at 0° C. for 3 hours, at room temperature for 30 minutes, and the reaction was quenched by addition of H2O (7 ml). The resulting mixture was stirred for 10 minutes and H2O (5 ml) and EtOAc (8 ml) were added. The mixture was then stirred overnight at room temperature. The solid was filtered off and washed with EtOAc. The organic layer was separated, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 4-(3-hydroxy-1-pheny-propyl)-1H-indole-3-carbonitrile LX as a white solid (377 mg, 67% yield).

Workup

  1. customthe reaction was quenched by addition of H2O (7 ml)
  2. stirringThe resulting mixture was stirred for 10 minutes
  3. additionH2O (5 ml) and EtOAc (8 ml) were added
  4. stirringThe mixture was then stirred overnight at room temperature
  5. filtrationThe solid was filtered off
  6. washwashed with EtOAc
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-4b8224e7ceb94bab9b1ac86a8696db14
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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