Diisobutylaluminum hydride → [3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol

HRID 242873Notes

Reaction equation

HRID 242873 reaction equation
C([O:3][C:4]([C:6]1[N:7]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:15]1([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([S:21]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)(=[O:22])=[O:23])[C:6]=2[CH2:4][OH:3])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 681575273-Phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 68156952[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanolYield 85.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (3.24 g, 7.72 mmol) in toluene (40 mL) at −78° C. and under a nitrogen atmosphere was added 1.0M DIBAL-H in toluene (23.2 mL, 23.2 mmol). The reaction mixture was stirred at −78° C. for 15 min then at −10° C. for 30 min. After re-cooling to −78° C., the reaction mixture was quenched with water (20 mL) then allowed to warm to RT. The mixture was partitioned between EtOAc and 1.0M HCl and the aqueous phase was extracted with additional EtOAc (×3). The combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane) affording the title compound as a white foam (2.49 g, 85%). LCMS (Method C): RT 4.77 min [M+Na]+ 400.1

Workup

  1. waitat −10° C. for 30 min
  2. temperatureAfter re-cooling to −78° C.
  3. customthe reaction mixture was quenched with water (20 mL)
  4. temperatureto warm to RT
  5. customThe mixture was partitioned between EtOAc and 1.0M HCl
  6. extractionthe aqueous phase was extracted with additional EtOAc (×3)
  7. washThe combined organic fractions were washed with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane)

Sources & evidence

ORD record
ord-ea44d798d2ae4933b79b4d8b395a5f18
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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