2-Methyl-2-cyano-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptane → 4-Ethyl-2-(4-fluorophenyl)-5-[(6,6-dimethyl-7-aminoheptyl)oxy]phenol
Reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:25])([C:23]#[N:24])[CH3:22])[C:12]([CH2:26][CH3:27])=[CH:11][C:10]=1[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pt]=O>[CH2:26]([C:12]1[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:25])([CH3:22])[CH2:23][NH2:24])=[CH:14][C:9]([OH:8])=[C:10]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:11]=1)[CH3:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(benzyloxy)-4-ethyl-2-(4-fluorophenyl)-5-[(6-methyl-6-cyanoheptyl)oxy]-benzene (485 mg) was dissolved in ethanol (15 mL) and added to a solution of platinum oxide (20 mg) in 10 mL ethanol in a Parr bottle. The bottle was pressurized to 55 psi with hydrogen and shaken for 20 hours. Additional catalyst (120 mg) was added and bottle shaken at 55 psi of hydrogen for an additional 18 hours. The solution was filtered through Celite and concentrated under vacuum to afford crude 4-ethyl-2-(4-fluorophenyl)-5-[(6,6-dimethyl-7-aminoheptyl)oxy]phenol (475 mg) as an oil. It was purified by chromatography on silica gel with chloroform/methanol eluant. The product fractions were combined and concentrated under vacuum (120 mg). NMR (CDCl3): 1.00, s, (6H); 1.15, t (3H); 1.33, m (2H); 1.44, m (2H); 1.77, m (2H); 2.55, q (2H); 2.74, s (2H); 3.92, t (2H); 6.52, s (1H); 6.96, s (1H); 7.11, d of d (2H); 7.43, d of d (2H). Mass Spec (EI), m/e=374.3 (M+H).
Workup
- filtrationThe solution was filtered through Celite
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-00686946d8ce465b9f1f26266a56e31d
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770259B2
Reaction notes
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