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CAS No. : | 125224-43-3 | MDL No. : | MFCD03839921 |
Formula : | C12H16FNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IBOPBHBOBJYXTD-JQWIXIFHSA-N |
M.W : | 209.26 | Pubchem ID : | 9855829 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 61.17 |
TPSA : | 32.26 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 2.19 |
Log Po/w (XLOGP3) : | 1.35 |
Log Po/w (WLOGP) : | 1.55 |
Log Po/w (MLOGP) : | 2.15 |
Log Po/w (SILICOS-IT) : | 2.54 |
Consensus Log Po/w : | 1.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.15 |
Solubility : | 1.47 mg/ml ; 0.00705 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.63 |
Solubility : | 4.91 mg/ml ; 0.0235 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.49 |
Solubility : | 0.0676 mg/ml ; 0.000323 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine; In dichloromethane; at 20℃; for 20.0h; | To a stirred solution of ((3S, 4R)-4-(4-fluorophenyl)piperidin-3-yl)methanol (1.00 g, 4.8 mmol) in methylene chloride (20 mL), was added triethylamine (1.30 mL, 9.3 mmol) and di-tert-butyl dicarbonate (1.50 g, 6.9 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 h and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and washed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL); dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (30% ethyl acetate in hexanes) to afford (3S,4/?)-te/f-butyl 4- (4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate in 92% yield (1.36 g) as a colorless solid: 1H NMR (300 MHz, CDCI3) 7.22 (d, J = 8.4 Hz, 2H), 7.08 (d, J = 8.4 Hz, 2H), 4.50-4.15 (m, 2H), 3.43 (s, 3H), 2.95-2.58 (m, 4H), 1.80-1.49 (m, 2H), 1.49 (s, 9H). |
90% | With sodium carbonate; In dichloromethane; water; for 0.5h;Cooling with ice; | To a mixture of <strong>[125224-43-3][(3S,4R)-4-(4-fluorophenyl)piperidine-3-yl]methanol</strong> (3.0 g, 14 mmol), sodium carbonate (6.1 g, 57 mmol), dichloromethane (40 mL) and water (40 mL) was added di-tert-butyl Bicarbonate (3.8 g, 17 mmol) under ice cooling, followed by stirring at the same temperature for 30 minutes. The reaction mixture was added to a mixed solution of dichloromethane and water, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1) to give the title compound (4.0 g, 90% yield). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.49 (9H, s), 1.61-1.71 (1H, m), 1.75-1.85 (2H, m), 2.51-2.56 (1H, m), 2.71 (1H, dd, J=11.3, 13.2 Hz), 2.78 (1H, br s), 3.24-3.29 (1H, m), 3.42-3.46 (1H, m), 4.20 (1H, br s), 4.36 (1H, d, J=11.7 Hz), 6.97-7.03 (2H, m), 7.13-7.18 (2H, m). |
In dichloromethane; for 2.0h; | [(3S,4R)-4-(4-Fluoro-phenyl)-piperidin-3-yl]-methanol (3.00 g, 14.3 mmol, 1 equiv) was suspended in CH2Cl2 (10 mL) and Boc anhydride (3.23 g, 14.8 mmol, 1.03 equiv) was added. This was stirred for 2 h then concentrated to give the crude, which was used in the next reaction without further purification. [ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | palladium; In ethanol; | Example 13 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine 1 g of (3S,4R)-trans-N-benzyloxycarbonyl-4-(4-fluorophenyl)-3-hydroxymethylpiperidine, is dissolved in 50 ml ethanol and 300 mg palladium catalyst over carbon in a hydrogen atmosphere is added. On completion of the reaction, it is filtered over Celite and concentrated to dryness. Yield: 87%; [alpha]d10=-24.3 (c 0.46, MeOH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | Preparation of compound 13a was accomplished by dissolving <strong>[125224-43-3]((3S,4R)-4-(4-fluorophenyl)piperidin-3-yl)methanol</strong> 12 (1.49 mmol, 0.311 g) in DMF (6.0 mL). Potassium carbonate (3.73 mmol, 0.515g) and ethyl iodide (1.63 mmol, 0.13 mL) were then added and the reaction was stirred overnight at room temperature. The reaction was then concentrated in vacuo and the crude residue was purified using flash chromatography 4 - 10 % MeOH (3M ammonia)/DCM to give ((3S,4R)-1-ethyl-4- (4-fluorophenyl)piperidin-3-yl)methanol (0.167g, 47% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; at 0 - 20℃; | Preparation of compound 13b was accomplished by dissolving ((3S,4R)-4-(4-fluorophenyl)piperidin-3- yl)methanol (0.765 mmol, 0.160 g) and sodium cyanoborohydride (2.30 mmol, 0.144 g) in THF (2.0 mL) and acetone (2.0 mL) at 0C. Acetic acid (3.06 mmol, 0.175 mL) was then added dropwise and the reaction was stirred overnight warming to room temperature. The reaction was neutralized with 2N NaOH and then extracted with ethyl acetate. The organic layer was washed 2x with NaCl, dried over MgSO4 and concentrated to give the desired product (0.15 g, 78% yield). |
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