Potassium Sodium Tartrate → 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-2-ethyl-butan-1-ol

HRID 472038Notes

Reaction equation

HRID 472038 reaction equation
C([O:3][C:4](=O)[C:5]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][N:16]=[C:17]([C:20]3[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:28][CH3:29])[CH:18]=2)[N:13]([C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[CH:12]=1)([CH2:8][CH3:9])[CH2:6][CH3:7])C.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[CH2:26]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:28][CH3:29])[C:20]=1[C:17]1[CH:18]=[C:19]2[C:11]([CH2:10][C:5]([CH2:6][CH3:7])([CH2:8][CH3:9])[CH2:4][OH:3])=[CH:12][N:13]([C:30]3[CH:31]=[CH:32][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:34][CH:35]=3)[C:14]2=[CH:15][N:16]=1)[CH3:27]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67152582HCID 67152582, compound

Product 1

HCID 582699632-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-2-ethyl-butan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-2-ethyl-butyric acid ethyl ester (100 mg, 0.19 mmol) in DCM (10 mL) at −78° C., DIBAL (1M solution in toluene, 0.95 mL, 0.9 mmol) is added and the mixture is allowed to gradually warm up room temperature, at which stirring is continued for 2 h. To the mixture, a saturated aqueous Rochelle's salt solution (10 mL) is added and stirring is continued for 1 h. The organic layer is separated and the aqueous is extracted with DCM. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue is purified by chromatography on silica gel (Hexane/EtOAc, 2:1) to afford 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-2-ethyl-butan-1-ol as colorless oil: LCMS m/z 483.21 (2.64 min)

Workup

  1. stirringstirring
  2. waitis continued for 1 h
  3. customThe organic layer is separated
  4. extractionthe aqueous is extracted with DCM
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography on silica gel (Hexane/EtOAc, 2:1)

Sources & evidence

ORD record
ord-38bc138bd7b94446ace3110441ba6ec0
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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