Hydrochloric Acid → HCID 58604044, compound

HRID 2113649Notes

Reaction equation

HRID 2113649 reaction equation
[CH2:1]([C@@:5]12[C@H:20]([CH2:21][CH2:22][CH3:23])[C:19](=[O:24])[CH:18]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:14]COC)=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4].Cl>CO.CCOC(C)=O>[CH2:1]([C@@:5]12[C@H:20]([CH2:21][CH2:22][CH3:23])[C:19](=[O:24])[CH:18]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([OH:14])=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58604078HCID 58604078, compound

Product 1

HCID 58604044HCID 58604044, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (rac)-(1S,8aR)-8a-butyl-6-(methoxymethoxy)-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (92 mg, 0.28 mmol) in methanol (1 mL) was treated with aqueous 2N HCl (0.42 mL, 0.84 mmol). The resulting mixture was stirred and gradually heated to 80° C. over 30 minutes, and then kept at 80° C. for an additional 30 minutes. After cooling, the mixture was diluted with EtOAc and washed with 5% NaHCO3. The aqueous portion was back-extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column, eluting with 5:1 hexane-EtOAc, to give (rac)-(1S,8aR)-8a-butyl-6-hydroxy-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as a white solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with 5% NaHCO3
  3. extractionThe aqueous portion was back-extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column
  9. washeluting with 5:1 hexane-EtOAc

Sources & evidence

ORD record
ord-56f61c242b114da9a378a89d17379cda
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…