Potassium Acetate → 7,8-diamino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372516Notes

Reaction equation

HRID 1372516 reaction equation
[NH2:1][C:2]1[C:14]([N+:15]([O-])=O)=[C:13]2[C:5]([C:6]3[C:11]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:22])[C:7]=3[CH3:23])=[CH:4][C:3]=1[F:24].CC([O-])=O.[K+]>C(O)C.[Pd]>[NH2:1][C:2]1[C:14]([NH2:15])=[C:13]2[C:5]([C:6]3[C:11]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:12]2)[CH2:10][CH2:9][C:8](=[O:22])[C:7]=3[CH3:23])=[CH:4][C:3]=1[F:24]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 99236627-amino-9a-butyl-6-fluoro-4-methyl-8-nitro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 98178757,8-diamino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A sample of 7-amino-9a-butyl-6-fluoro-4-methyl-8-nitro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (106 mg, 0.32 mmol) was dissolved in ethanol (13 mL) with slight warming. After cooling to room temperature, the solution was treated with KOAc (31 mg, 32 mmol) and 10% palladium on carbon (31 mg), and the resulting mixture was stirred under an atmosphere of hydrogen for 3.25 hours. The mixture was filtered through a pad of silica gel, washing the product off with 5% MeOH in CH2Cl2. The filtrate and washings were evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 1:1 hexanes-EtOAc. The major UV visible band was eluted with 5% MeOH in CH2Cl2, the eluant was concentrated under vacuum, and the residue was lyophilized from benzene to afford 7,8-diamino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (70 mg, 72%) as an amorphous solid.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. washwashing the product off with 5% MeOH in CH2Cl2
  3. customThe filtrate and washings were evaporated under vacuum
  4. customThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  5. washThe major UV visible band was eluted with 5% MeOH in CH2Cl2
  6. concentrationthe eluant was concentrated under vacuum

Sources & evidence

ORD record
ord-a8a21da4fd294d428fefb6cbd9b85f56
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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