Potassium Sodium Tartrate → HCID 67152539, compound

HRID 472057Notes

Reaction equation

HRID 472057 reaction equation
C(O[C:4](=[O:36])[CH:5]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][N:15]=[C:16]([C:19]3[C:24](C)=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:26])[CH:17]=2)[N:12]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[CH:11]=1)[CH2:6][CH2:7][CH3:8])C.[CH3:37][CH:38](C[AlH]CC(C)C)C.[C@H:46](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>>[CH2:23]([C:24]1[CH:38]=[CH:37][CH:21]=[C:20]([CH2:26][CH3:46])[C:19]=1[C:16]1[CH:17]=[C:18]2[C:10]([CH2:9][CH:5]([CH2:6][CH2:7][CH3:8])[CH2:4][OH:36])=[CH:11][N:12]([C:27]3[CH:28]=[CH:29][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:32]=3)[C:13]2=[CH:14][N:15]=1)[CH3:22]

Participants

4

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 67152412HCID 67152412, compound

Product 1

HCID 67152539HCID 67152539, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-pentanoic acid ethyl ester (120 mg, 0.23 mmol) at −78° C., DIBAL (1M sol in toluene, 1.0 mL, 1.0 mmol) is added, and the mixture is stirred for 3 h at −78° C. The temperature of the mixture is allowed to gradually warm up to room temperature. To the mixture, a saturated aqueous Rochelle's salt solution (10 mL) is added, and the resultant suspension is stirred for 2 h at room temperature. The organic phase is separated, and the aqueous portion is extracted with DCM. The combined organic extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure, and the residue purified by chromatography on silica gel (hexane-EtOAc, 1:1) to afford 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-pentan-1-ol as colorless oil.

Workup

  1. temperatureto gradually warm up to room temperature
  2. customThe organic phase is separated
  3. extractionthe aqueous portion is extracted with DCM
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed under reduced pressure
  7. customthe residue purified by chromatography on silica gel (hexane-EtOAc, 1:1)

Sources & evidence

ORD record
ord-eb2f52f16a684b45b6afea88ce20d2e6
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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