Hydrochloric Acid → HCID 86587280, compound

HRID 7870Notes

Reaction equation

HRID 7870 reaction equation
[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][CH:19]=[O:20])[C:15](=[O:21])[C:14]([CH3:22])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:23]COC)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl>CO.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][CH:16]([CH2:18][CH:19]=[O:20])[C:15](=[O:21])[C:14]([CH3:22])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86587281HCID 86587281, compound

Product 1

HCID 86587280HCID 86587280, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg) in methanol (1 mL) was diluted with 2N HCl (0.36 mL, 0.72 mmol). The resulting mixture was stirred at room temperature for 30 minutes followed by heating in an oil bath at 80° C. for 40 minutes. On cooling to room temperature, crystals formed. The mixture was diluted with EtOAc and washed with 5% NaHCO3 and 1N HCl. The aqueous washes were back-extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by PLC on a 0.1×20×20 cm silica gel GF plate, using 2:1 hexanes-EtOAc as developing solvent, to afford (2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg).

Workup

  1. temperatureby heating in an oil bath at 80° C. for 40 minutes
  2. temperatureOn cooling to room temperature
  3. customcrystals formed
  4. washwashed with 5% NaHCO3 and 1N HCl
  5. extractionThe aqueous washes were back-extracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by PLC on a 0.1×20×20 cm silica gel GF plate

Sources & evidence

ORD record
ord-91f58590443c4623a63d18722cfb6815
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

Loading…