Hydrochloric Acid → (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7873Notes

Reaction equation

HRID 7873 reaction equation
[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][C:19](=[O:22])[CH2:20][OH:21])[C:15](=[O:23])[C:14]([CH3:24])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:25]COC)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl>CO>[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][C:19](=[O:22])[CH2:20][OH:21])[C:15](=[O:23])[C:14]([CH3:24])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:25])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67398080(2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 10268956(2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (24 mg, 0.06 mmol) in methanol (1 mL) was treated with 2N HCl (0.36 mL, 0.18 mmol) and the resulting solution was heated at reflux for 20 minutes. After cooling, the mixture was concentrated under vacuum to a residue that was dissolved in EtOAc (60 mL) and washed with 5% NaHCO3 (30 mL). The aqueous phase was back-extracted with EtOAc (30 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by PLC, using 1:1 hexanes-EtOAc as developing solvent, to afford (2RS,9aSR)-9a-butyl-7-hydroxy-2-(3-hydroxy-2-oxopropyl)-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 20 minutes
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under vacuum to a residue that
  5. dissolutionwas dissolved in EtOAc (60 mL)
  6. washwashed with 5% NaHCO3 (30 mL)
  7. extractionThe aqueous phase was back-extracted with EtOAc (30 mL)
  8. washThe combined organics were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated under vacuum
  12. customThe residue was purified by PLC

Sources & evidence

ORD record
ord-b15b3e94ee9748ad969eea6cc232a478
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

Loading…