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CAS No. : | 189442-87-3 | MDL No. : | MFCD08689955 |
Formula : | C14H25NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZQZVWDXMUCTNRI-UHFFFAOYSA-N |
M.W : | 271.35 | Pubchem ID : | 16218276 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 76.85 |
TPSA : | 55.84 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 3.44 |
Log Po/w (XLOGP3) : | 2.18 |
Log Po/w (WLOGP) : | 2.21 |
Log Po/w (MLOGP) : | 1.85 |
Log Po/w (SILICOS-IT) : | 1.93 |
Consensus Log Po/w : | 2.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.5 |
Solubility : | 0.859 mg/ml ; 0.00316 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.99 |
Solubility : | 0.28 mg/ml ; 0.00103 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.36 |
Solubility : | 1.18 mg/ml ; 0.00435 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.54 |
Signal Word: | Danger | Class: | 8,6.1 |
Precautionary Statements: | P261-P280-P301+P310-P305+P351+P338 | UN#: | 2922 |
Hazard Statements: | H301-H315-H318-H335 | Packing Group: | Ⅲ |
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 lithium hydroxide; water In methanol at 25℃; for 16 h; | A mixture of the compound of formula LB (4.1Og, 15.1mmol) and lithium hydroxide (2.17g, 90.6mmol) in methanol (3OmL)ZH2O (2OmL) was stirred at a temperature of about 250C for 16h. After evaporation to dryness, the residue was partitioned between DCM and brine. The organic layer was separated, dried (MgSO4), filtered, and concentrated under reduced pressure to provide 3.38g of the compound of formula LC as a white solid (yield 92.0percent).The identity of the compound of formula LC, l-(teτt-butoxycarbonyl)- 4-methylpiperidine-4-carboxylic acid, was confirmed using 1H NMR and LC/MS.Compound LC: 1H NMR: δH (400 MHz, CDCl3): 3.60-3.70 (2H, m), 3.03-3.09 (2H, m)2.05-2.08 (2H, m), 1.45 (9H, s), 1.36-1.45 (2H, m), 1.27 (3H, m); LC/MS (100percent, tr = 2.500 min), m/z = 266.1 [M + Na]+ (CaIc: 243). |
75% | Stage #1: With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 48 h; Stage #2: With hydrogenchloride In water |
Method W: 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid 2.0 M sodium hydroxide (20 ml) was added to 1-tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (4 g, 14.76 mmol) in tetrahydrofuran (40 ml) and methanol (5 ml). The solution was stirred at room temperature for 48 hours. The reaction mixture was extracted with ethyl acetate. The aqueous layer was acidified to pH 1-2 with a concentrated solution of HCl. The acid was extracted with EtOAc. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the desired compound (2.7 g, 75percent yield). 1H NMR (CDCl3, 400 MHz) δ 1.29 (3H, s), 1.36-1.48 (2H, m), 1.47 (9H, s), 2.09 (2H, dt), 3.08 (2H, t), 3.79 (2H, br d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 2.5 h; Inert atmosphere | Ethyl N-Boc-piperidine-4-carboxylate (10.00 g, 36.92 mmol) was dissolved in THF(100 mL) and cooled to -78°C. LDA (47 mmol, 23 mL) was added and the reaction stirred for 1 h. Iodomethane (81.25 mmol, 5.08 mL) was then added and the reaction stirred for a further lh before removing the cold bath and allowing the reaction to warm to r.t. for 30 min. The reaction was quenched with NH4C1 (sat) and partitioned with EtOAc, the organics were extracted and dried (MgS04) and concentrated in vacuo, (quantitative yield). 1H NMR (400 MHz, DMSO- d6) δ: 4.11 (q, J 7.1 Hz, 2 H), 3.61 (dt, J 13.4 Hz, J 4.5 Hz, 2 H), 2.95 (d, J 0.3 Hz, 2 H), 1.91 (d, J 13.6 Hz, 2 H), 1.39 (s, 9 H), 1.31 (m, 2 H), 1.19 (m, 3 H), 1.15 (s, 3 H). |
100% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Stage #2: at 20℃; for 1.5 h; |
Ethyl N-Boc-piperidine-4-carboxylate (10.00 g, 36.92 mmol) was dissolved inTHF (100 mL) and cooled to -78°C. LDA (47 mmol, 23 mL) was added and the reactionstirred for 1 h. lodomethane (81.25 mmol, 5.08 mL) was then added and the reaction stirred for a further lh before removing the cold bath and allowing the reaction to warm to r.t. for 30 mm. The reaction was quenched with sat. aq. NH4C1 and partitioned with EtOAc, the organics were extracted and dried (MgSO4) and concentrated in vacuo,(quantitative yield). 1H NMR (400 MHz, DMSO- d6) ö: 4.11 (q, J7.1 Hz, 2 H), 3.61 (dt, J13.4 Hz, J 4.5 Hz, 2 H), 2.95 (d, J 0.3 Hz, 2 H), 1.91 (d, J 13.6 Hz, 2 H), 1.39 (s, 9 H),1.31 (m, 2 H), 1.19 (m, 3 H), 1.15 (s, 3 H). |
100% | Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -40℃; for 1 h; Stage #2: at -40 - 20℃; for 14 h; |
The compound was prepared following a procedure outlined in PCT Publication No. WO 01/40217. 1-tert-Butyl 4-ethyl piperidine-l,4-dicarboxylate (7.12 g, 27.7 mmol) was dissolved in THF (30 mL) and cooled to -40 °C. LHMDS (55.3 ml, 55.3 mmol) was added slowly and the solution was stirred at -40 °C for 1 hour. Iodomethane (3.45 ml, 55.3 mmol) was added and the reaction mixture was warmed to ambient temperature and stirred for 14 hours. The reaction was quenched with water and saturated NaHCO3. After diluting with methylene chloride, the layers were separated. The aqueous layer was washed twice with methylene chloride, and the combined organic layers were washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to provide the desired product as an oil (quantitative). 1H NMR (400 MHz, CDCl3) δ 4.16 (q, 2H), 3.83-3.70 (m, 2H), 3.03-2.94 (m, 2H), 2.11-2.02 (m, 2H), 1.45 (s, 9H), 1.41-1.30 (m, 2H), 1.26 (t, 3H), 1.20 (s, 3H). |
76.8% | Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 2.75 h; Stage #2: at -78 - 25℃; for 16 h; |
To a mixture of iV,jV-diisopropylamme (6.8ImL, 48.6mmol) in THF (10OmL) at a temperature of O0C was added dropwise a mixture of 1.6N n-butyl lithium (Sigma-Aldrich) in THF (30.4mL, 48.6mmol). The resulting mixture was stirred at O0C for 15 min. After cooling to a temperature of -780C, a mixture of the compound of formula LA (1-tert-butyl 4-ethyl piperidine-l,4-dicarboxylate, 10. Og, 38.9mmol, Sigma-Aldrich) in THF (5OmL) was added dropwise over a 30min period. After being stirred at -780C for 2h, a mixture of methyl iodide (4.84mL, 77.7mmol) in THF (3OmL) was added dropwise at -780C. The mixture was allowed to warm to a temperature of about 250C for 16h. After quenching with saturated aqueousNH4Cl, the mixture was partitioned between THF and saturated aqueous NH4Cl. The organic layer was separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was chromatographed (COMBIFLASH) with a gradient of from 0percent:100percent EtOAc:hexanes to 50percent:50percent EtOAc:hexanes to provide, after concentration under reduced pressure, 8.1Og of the compound of formula LB as a pale yellow solid (yield 76.8percent).The identity of the compound of formula LB, l-tert-buty\\ 4-ethyl 4-methylpiperidine- 1 ,4-dicarboxylate, was confirmed using 1H NMR.Compound LB: 1H NMR: δH (400 MHz, CDCl3): 4.16 (2H, q, J=7.1Hz), 3.76 (2H, br), 2.95-3.01 (2H, m), 2.05-2.08 (2H, m), 1.45 (9H, s), 1.32-1.43 (2H, m), 1.26 (3H, t, J=7. IHz), 1.20 (3H, s). |
75% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.666667 h; Inert atmosphere Stage #2: at 0 - 20℃; for 5 h; |
tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate To tert-butyl-4-ethyl piperidine-1,4-dicarboxylate (10.03 g, 39.0 mmol), dissolved in THF (50 mL) and cooled to 0° C. in an ice bath under nitrogen, was added dropwise LDA (2M solution in THF; 25.0 mL, 50 mmol). The mixture was stirred at 0° C. for 40 minutes. Iodomethane (3.2 mL, 51 mmol) was then added, and the mixture was stirred at 0° C. for 3 h before warming to r.t. The reaction mixture was left to stand at r.t. for 2 h. EtOAc (150 mL) was added and the mixture was washed with brine (2*100 mL). The organic layer was separated, dried (Na2SO4), and filtered under reduced pressure. The solvent was removed in vacuo to yield a brown oil which was purified by flash column chromatography on silica, using 100percent isohexane to 100percent EtOAc, followed by concentration in vacuo, to afford the title compound (7.92 g, 75percent) as an orange oil. δH (300 MHz, DMSO-d6) 4.10 (q, J 7.1 Hz, 2H), 3.60 (dt, J 13.6, 4.4 Hz, 2H), 2.94 (br t, J 11.7 Hz, 2H), 1.95-1.84 (m, 2H), 1.39 (s, 9H), 1.30 (ddd, J 14.0, 10.2, 4.1 Hz, 2H), 1.18 (t, J 7.1 Hz, 3H), 1.14 (s, 3H). |
65% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75 h; Stage #2: at -78 - 20℃; for 6 h; |
A solution of O1-tert-butyl O4-ethyl piperidine-1,4-dicarboxylate (1.5 g, 5.84 mmol) in THF (25 mL) was cooled to -78° C. followed by dropwise addition of LDA (1.80 M in THF, 6.5 mL, 11.68 mmol) at -78° C. The resulting mixture was stirred at the same temperature for 45 minutes followed by addition of MeI (1.2 mL, 17.52 mmol) at -78° C. The temperature of the reaction mixture was slowly raised up to rt and left to stir at rt for 6 h. The reaction mixture was then cooled to 0° C., quenched by dropwise addition of saturated NH4Cl solution (50 mL) and extracted with EtOAc (3.x.100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 2percent EtOAc:hexane to obtain the desired product as a liquid (1.0 g, 65percent). |
65% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75 h; Stage #2: at -78 - 20℃; for 6 h; |
A solution of O1-tert-butyl O4-ethyl piperidine-1,4-dicarboxylate (1.5 g, 5.84 mmol) in THF (25 mL) was cooled to -78° C. followed by dropwise addition of LDA (1.80 M in THF, 6.5 mL, 11.68 mmol) at -78° C. The resulting mixture was stirred at -78° C. for 45 min followed by addition of methyl iodide (1.2 mL, 17.52 mmol). The temperature was slowly raised up to RT and left at RT for 6 h. The reaction was cooled to 0° C. and quenched by the dropwise addition of saturated NH4Cl solution (50 mL). The reaction was extracted with EtOAc (3*100 mL). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by chromatography on silica eluting with 2percent EtOAc in hexane gave i (1.0 g, 65percent). |
60% | Stage #1: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -70℃; for 1.25 h; Stage #2: at -70 - 20℃; |
Method V: 1-tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate Butyllithium 2.5 M in hexanes (15 ml, 37.5 mmol) was added dropwise over 15 minutes to an ice cold solution of diisopropylamine (5.35 ml, 37.5 mmol) in tetrahydrofuran (200 ml). The solution was stirred at 0° C. for 15 minutes, then cooled to -70° C. A solution of 1-tert-butyl 4-Ethyl piperidine-1,4-dicarboxylate (9.0 g, 35 mmol) in tetrahydrofuran (30 ml) was added dropwise over 15 minutes. The reaction mixture was stirred at -70° C. for a further 1 hour. A solution of methyl iodide (3.2 ml, 52 mmol) in tetrahydrofuran (30 ml) was added dropwise over 15 minutes. The reaction mixture was stirred at -70° C. for a further 2 hours and then allowed to warm up to room temperature overnight. The reaction mixture was partitioned between EtOAc and a saturated solution of ammonium chloride. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the desired compound (5.7 g, 60percent yield). 1H NMR (CDCl3, 400 MHz) δ 1.21 (3H, s), 1.28 (3H, t), 1.32-1.42 (2H, m), 1.47 (9H, s), 2.08 (2H, dt), 2.95-3.03 (2H, m), 3.79 (2H, dt), 4.18 (2H, q). |
52% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h; Stage #2: for 1 h; |
To a stirred solution ofN-Boc-ethylisonipecotate 17 (503.4 mg, 1.96 mmols) in dry THF(10.0 mL), cooled at -78 °C, freshly prepared solution of lithiumdiisopropyl amide (0.5 M in THF,4.70 mL) was added. After stirring the reaction mixture for 1 h, methyl iodide(0.2 mL, 2.94 mmols) was added and the stirring continued for another hourbefore the reaction mixture was quenched with saturated aqueous NH4Clsolution. The reaction mass was extracted with ethylacetate and the combinedorganic layer was dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure and the crude product was purifiedby silica gel column chromatography to obtain the above titled compound 18 (280.5 mg) as gummy liquid in 52percentyield. 1H - NMR (CDCl3): d 4.16 (q, J= 7.1 Hz, 2H), 3.88-3.72 (m, 2H), 3.10-2.92 (m, 2H), 2.13-2.02 (m, 2 H),1.42 (s,9H), 1.45-1.32 (m, 2H), 1.25 (t, J =7.1 Hz, 3H) , 1.19 (s, 3H ).Mass (m/z): 272.4 (M+H)+ |
17.7 g | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; hexane at -60 - -20℃; for 0.833333 h; Inert atmosphere Stage #2: at -50℃; for 0.833333 h; |
To a -60 °C solution of 1-(tert-butyl) 4-ethyl piperidine-1,4-dicarboxylate (15.52 g,60.31 mmol) in THF (100 ml) was added LDA(2 M solution in THF/Hex, 45.00 mL, 90.00 mmol)dropwise under nitrogen atmosphere. The resulting mixture was allowed to warm to -20 °C and stirred for 50 mm. The mixture was cooled to -50 °C, and a solution of CH3I (8.56 g, 60.31 mmol) in THF (20 mL) was added dropwise. The resulting mixture was stirred for 50 mm at this temperature. The reaction mixture was carefully quenched with sat. aq. NH4C1 (80 mL), extractedwith EA (100 mL, 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 1-(tert-butyl) 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (17.70 g) which was used without any further purification. MS: m/z 216 (M+H-56) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 6 h; | 4M Solution of hydrogen chloride in 1,4-dioxane (3 mL) was added to a solution of 1- tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (0.34 g, 1.25 mmol) in ethanol (4 mL) and the resulting mixture was stirred for 6 hours at room temperature. The solvents were evaporated and the residue was treated with diethyl ether, filtered and washed with diethyl ether to yield the hydrochloride salt of the title compound (0.3 g,99percent) as a white solid.LRMS (mlz): 172 (M+1)+. |
59.6% | With hydrogenchloride In 1,4-dioxane at 0 - 20℃; for 18 h; Inert atmosphere | To a solution of Intermediate 25 ( 11.0 g, 40.5 mmol) dissolved in 1,4-Dioxane (30.0 mL) at 0-5°C was added HC1 (15.2 mL, 4 M in 1,4-dioxane) the mixture was allowed to warm to r.t. and stirred for 18h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6percent). 1H NMR (DMSO-d6) δ: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H). |
59.6% | With hydrogenchloride In 1,4-dioxane at 0 - 20℃; for 18 h; | To a solution of Intermediate 37 (11.0 g, 40.5 mmol) dissolved in 1 ,4-dioxane (30.0 mL) at 0-5°C was added HC1 (15.2 mL, 4 M in 1,4-dioxane). The mixture was allowed to warm to r.t. and stirred for 1 8h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6percent). 1H NMR (DMSO-d6) ö: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H). |
0.90 g | With hydrogenchloride In 1,4-dioxane at 20℃; for 0.5 h; | Ethyl 4-methylpiperidine-4-carboxylate hydrochloride (ii) To an ice-cold solution of i (1 g, 3.68 mmol) in 1,4-dioxane (10 mL) was added HCl-1,4-dioxane (4.0 M, 15 mL) solution and stirred at RT for 30 min. The solvent was evaporated to obtain ii (0.90 g). MS: 172.16 [M+H]+. |
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