Hydrochloric Acid → HCID 11472382, compound

HRID 2118394Notes

Reaction equation

HRID 2118394 reaction equation
[CH2:1]([CH:3]1[CH2:29][CH:6]2[CH:7]([C:19]3[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][CH:20]=3)[O:8][C:9]3[CH:10]=[CH:11][C:12]([O:15]COC)=[CH:13][C:14]=3[CH:5]2[CH2:4]1)[CH3:2].Cl.CCOC(C)=O.CCOC(C)=O.CCCCCC>C1COCC1>[CH2:1]([C@H:3]1[CH2:29][C@H:6]2[C@@H:7]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[O:8][C:9]3[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][C:14]=3[C@H:5]2[CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226206Ethyl acetate hexaneHCID 68725707HCID 68725707, compound

Product 1

HCID 11472382HCID 11472382, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve alkyl cyclopentane 38 (109 mg, 0.27 mmol) in THF (4 mL) then add 3 M HCl (1.0 mL). Stir the reaction at room temperature overnight. Dilute the reaction with EtOAc and wash with saturated aqueous sodium bicarbonate and brine. Extract the aqueous layer with EtOAc (1×). Combine the organic extracts, dry (Na2SO4), filter and concentrate in vacuo. Purify by flash chromatography (10 g SiO2, dry loading on 700 mg silica, 40 ml/min, 0-30% EtOAc/Hexane over 25 minutes and then 30% EtOAc/hexane for 7 minutes) to afford 56 mg (0.18 mmol, 68%) of alkyl cyclopentane 39 as a white solid. HRMS(ES+) calcd for C20H26NO3: 328.1913; found: 328.1906 (M+NH4). HPLC (Zorbax C18 column; 10 to 100% CH3CN/H2O for 10 min then 100% CH3CN for 5 min; 1 mL/min; tr 9.33 min).

Workup

  1. customthe reaction at room temperature overnight
  2. additionDilute
  3. washwash with saturated aqueous sodium bicarbonate and brine
  4. extractionExtract the aqueous layer with EtOAc (1×)
  5. dry with materialCombine the organic extracts, dry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by flash chromatography (10 g SiO2
  9. dry with materialdry loading on 700 mg silica, 40 ml/min, 0-30% EtOAc/Hexane over 25 minutes

Sources & evidence

ORD record
ord-70c8904b7cf146bdb46a21e272544246
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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