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CAS No.: | 389573-45-9 |
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Name: | ent-Paroxol |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C13H18FNO |
Molecular Weight: | 223.29 |
Synonyms: | ((3R,4S)-4-(4-Fluorophenyl)-1-methylpiperidin-3-yl)methanol;ent-Paroxol; |
Density: | 1.092±0.06 g/cm3(Predicted) |
Melting Point: | 98-100°C |
Boiling Point: | 300.3±42.0 °C(Predicted) |
PSA: | 23.47000 |
LogP: | 1.79120 |
(3R, 4S)-trans-3-carbomethoxy-4-(4-fluorophenyl)-N-methyl-piperidine
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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Stage #1: (3R, 4S)-trans-3-carbomethoxy-4-(4-fluorophenyl)-N-methyl-piperidine With lithium aluminium tetrahydride In tetrahydrofuran at -30 - -25℃; for 0.5h; Stage #2: With water at 25 - 30℃; for 1h; |
formaldehyd
(3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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In ethanol; water; toluene |
2,6-dichlorostyrene
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In hexane; 1,3,5-trimethyl-benzene at 110℃; for 24h; Inert atmosphere; | 92% |
(E)-3-(4-fluorophenyl)acryloyl chloride
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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With triethylamine In dichloromethane at -5℃; for 0.166667h; | 90% |
Sesamol
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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With hydrogenchloride; sodium; triethylamine; benzenesulfonyl chloride 1.) toluene, 0 deg C, 72 h, 2.) toluene, 4-methyl-2-pentanol, reflux, 4 h; Multistep reaction; |
4-methoxy-phenol
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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With hydrogenchloride; sodium; triethylamine; benzenesulfonyl chloride 1.) toluene, 0 deg C, 72 h, 2.) toluene, 4-methyl-2-pentanol, reflux, 4 h; Multistep reaction; |
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
(3R,4S)-3-bromomethyl-4-(4-fluorophenyl)-1-methylpiperidine
Conditions | Yield |
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With dibromo sulfoxide In acetonitrile for 1h; Heating; |
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
4-(4-fluorophenyl)-1,5-dimethyl-1,2,5,6-tetrahydropyridine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: SOBr2 / acetonitrile / 1 h / Heating 2: DBU / toluene / 3 h / 120 - 125 °C 3: KF; Al2O3 / 0.5 h / microwave irradiation View Scheme |
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
(4S)-4-(4-fluorophenyl)-1-methyl-3-methylenepiperidine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: SOBr2 / acetonitrile / 1 h / Heating 2: DBU / toluene / 3 h / 120 - 125 °C View Scheme |
(-)-trans-4-(4'-Fluorophenyl)-3-hydroxymethyl-N-methyl-piperidine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 1.) benzenesulfonyl chloride, triethylamine, 2.) sodium, 3.) hydrochloric acid / 1.) toluene, 0 deg C, 72 h, 2.) toluene, 4-methyl-2-pentanol, reflux, 4 h 2: 1.) BrCN, 2.) LiAlH4 View Scheme |