Acetic Acid → 7-amino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[C:6]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH3:17])[CH2:5]2.C(O)(=O)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8]([C:7]3[C:6]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:5]2)[CH2:13][CH2:14][C:15](=[O:18])[C:16]=3[CH3:17])=[CH:9][C:10]=1[F:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The diketone from step 1 (0.51 g, 1.73 mmol) was treated with acetic acid (5 mL,) and aqueous 6N HCl (5 mL). The resulting solution was stirred and heated in an oil bath at 100° C. for 1.5 hours. After cooling to room temperature, the mixture was poured into a slurry of solid NaHCO3 in CH2Cl2, then filtered through a pad of silica gel and the product was washed off with EtOAc. The filtrate and washings were concentrated under vacuum. The residue was purified by flash chromatography on a Biotage 40M KP-Sil column, eluting with 4:1 to 3:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to provide 7-amino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.40 g, 83%) as a yellow solid
Workup
- temperatureAfter cooling to room temperature
- filtrationfiltered through a pad of silica gel
- washthe product was washed off with EtOAc
- concentrationThe filtrate and washings were concentrated under vacuum
- customThe residue was purified by flash chromatography on a Biotage 40M KP-Sil column
- washeluting with 4:1 to 3:1 hexanes-EtOAc
- additionThe product containing fractions
- customwere evaporated under vacuum
Sources & evidence
- ORD record
- ord-dd59082a89f1496bb23a03aea1bb415a
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157604B2
Reaction notes
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