Cyclopentanol → HCID 15895873, compound

HRID 1884573Notes

Reaction equation

HRID 1884573 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:41]1[CH:42]=[C:43]([S:47][C:48]2[C:53]([O:54][CH2:55][CH2:56][CH2:57][C:58]3[CH:63]=[CH:62][N:61]=[CH:60][CH:59]=3)=[CH:52][CH:51]=[CH:50][N:49]=2)[CH:44]=[CH:45][CH:46]=1>C1COCC1>[CH:1]1([O:6][C:45]2[CH:44]=[C:43]([S:47][C:48]3[C:53]([O:54][CH2:55][CH2:56][CH2:57][C:58]4[CH:63]=[CH:62][N:61]=[CH:60][CH:59]=4)=[CH:52][CH:51]=[CH:50][N:49]=3)[CH:42]=[CH:41][CH:46]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12051151HCID 12051151, compound

Product 1

HCID 15895873HCID 15895873, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentanol (0.11 g, 1.3 mmol) and triphenylphosphine (0.47 g, 1.8 mmol) are dissolved in THF (15 ml), and thereto are successively add with stirring diisopropyl azodicarboxylate (0.26 g, 1.3 mmol) and 2-(3-hydroxyphenylthio)-3-[3-(pyridin-4-yl)propoxy]pyridine (0.30 g, 0.89 mmol) obtained in Example 13. The mixture is further stirred at room temperature for 30 minutes, and the reaction solution is concentrated under reduced pressure. The residue is extracted with a 10% aqueous hydrochloric acid solution (30 ml), and the aqueous layer is washed with chloroform (30 ml×2), and the pH value thereof is adjusted to pH 12 with potassium carbonate. The mixture is extracted with ethyl acetate (50 ml×2), and the organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol) to give the title compound (0.26 g) as a colorless oil.

Workup

  1. concentrationthe reaction solution is concentrated under reduced pressure
  2. extractionThe residue is extracted with a 10% aqueous hydrochloric acid solution (30 ml)
  3. washthe aqueous layer is washed with chloroform (30 ml×2)
  4. extractionThe mixture is extracted with ethyl acetate (50 ml×2)
  5. washthe organic layer is washed with a saturated brine (50 ml×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-e2e10fdc8061457c994c7c2c310fe0b4
Source dataset
uspto-grants-2004_07
Patent number
US06765095B2

Reaction notes

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