t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyloxy)tetrahydropyridine-1(2H)-carboxylate → piperidin-4-yl(2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

HRID 458750Notes

Reaction equation

HRID 458750 reaction equation
[F:1][C:2]1([F:31])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:30])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[O:9])[CH2:3]1>Cl.CO>[F:31][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:30])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

3

Reactant 1

HCID 69078802t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyloxy)tetrahydropyridine-1(2H)-carboxylate

Product 1

HCID 69766623piperidin-4-yl(2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

162 Milligrams of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoyloxy)tetrahydropyridine-1(2H)-carboxylate was dissolved in 5 ml of 10% hydrochloric acid-methanol, stirred for 12 hours, and the solvent was distilled off under reduced pressure. The residue was diluted with water, washed with diethyl ether and a saturated aqueous sodium hydrogencarbonate solution was added to the aqueous layer to render it alkaline. Following an extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 104 mg of the title compound was obtained as a colorless, foamy substance.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was diluted with water
  3. washwashed with diethyl ether
  4. additiona saturated aqueous sodium hydrogencarbonate solution was added to the aqueous layer
  5. extractionan extraction with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-5cef6702d58541f6ae9d85b67fc2f148
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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