7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one → 7-amino-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372520Notes

Reaction equation

HRID 1372520 reaction equation
C([NH:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[C:10]=3[Br:23])=[CH:7][C:6]=1[F:24])(=O)C>CO.Cl>[NH2:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[C:10]=3[Br:23])=[CH:7][C:6]=1[F:24]

Participants

4

Reactant 1

HCID 179727237-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 99464917-amino-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 48.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-(acetylamino)-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg, 0.1 mmol) in methanol (0.5 mL) was diluted with aqueous 6N HCl (0.5 mL). The resulting mixture was stirred in a capped flask and heated in an oil bath at 80° C. for 40 minutes. After cooling, the mixture was partitioned between water and EtOAc. The organic solution was washed with aqueous 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil. The oil ws purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 2:1 hexanes-EtOAc. The major UV visible band was eluted with 5% MeOH in CH2Cl2, the eluant was evaporated under vacuum, and the residue was lyophilized from benzene to provide 7-amino-4-bromo-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg, 47%) as an amorphous solid.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between water and EtOAc
  3. washThe organic solution was washed with aqueous 5% NaHCO3, water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum to an oil
  7. customThe oil ws purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  8. washThe major UV visible band was eluted with 5% MeOH in CH2Cl2
  9. customthe eluant was evaporated under vacuum

Sources & evidence

ORD record
ord-25b49c51a2694a73b498d73925b831b8
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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