HCID 68705549, compound → HCID 11208678, compound

HRID 2118389Notes

Reaction equation

HRID 2118389 reaction equation
COC[O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21]COC)=[CH:17][CH:16]=3)[CH:9]3[CH2:25][C:26](=[O:28])[CH2:27][CH:8]3[C:7]=2[CH:6]=1>C1COCC1.Cl.CCOC(C)=O>[OH:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][C@@H:10]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[C@H:9]3[CH2:25][C:26](=[O:28])[CH2:27][C@H:8]3[C:7]=2[CH:6]=1

Participants

5

Reactant 1

HCID 68705549HCID 68705549, compound

Product 1

HCID 11208678HCID 11208678, compoundYield 102.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a solution of cyclopentanone 23 (384 mg, 1.0 mmol) in 10 mL of THF and 8 mL of 3 M HCl overnight. Dilute the solution with EtOAc. Separate the aqueous solution and extract 2× with EtOAc. The combined organic solutions were washed with saturated aqueous sodium bicarbonate, brine, dried over Na2SO4, filtered, and concentrated to afford 304 mg of cyclopentanone 24. The material was purified by preparative chiral chromatography (Chiralpak AD, 65/35 heptane/ethanol).

Workup

  1. customSeparate the aqueous solution
  2. extractionextract 2× with EtOAc
  3. washThe combined organic solutions were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46cea839e20a4aecbc8b201dd7377cad
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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