Ethanol → HCID 60026335, compound

HRID 400681Notes

Reaction equation

HRID 400681 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([C:13]([CH3:32])([CH3:31])[CH2:14][C:15]([CH2:21][C:22]2[NH:30][C:25]3=[CH:26][N:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)([OH:20])[C:16]([F:19])([F:18])[F:17])[CH:10]=[CH:11][CH:12]=1.C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[F:19][C:16]([F:17])([F:18])[C:15]([OH:20])([CH2:21][C:22]1[NH:30][C:25]2=[CH:26][N:27]=[CH:28][CH:29]=[C:24]2[CH:23]=1)[CH2:14][C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH:2]=[O:1])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 702EthanolHCID 22033616Pyridinium.p-toluenesulfonateHCID 60026368HCID 60026368, compound

Product 1

HCID 60026335HCID 60026335, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-[1,3]dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol (160 mg, 0.36 mmol), 2 mL of ethanol, 1 mL of water, and pyridinium p-toluenesulfonic acid (200 mg, 0.8 mmol) was stirred at room temperature for 14 hours and then concentrated in vacuo to remove ethanol. The residue was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with aqueous saturated sodium bicarbonate solution and brine, and dried over sodium sulfate. Removal of the solvent in vacuo afforded 134 mg (95% yield) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove ethanol
  3. additionThe residue was diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with aqueous saturated sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-151ff34c2b3445fcaadb8dc1777477a4
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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