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CAS No. : | 85908-96-9 | MDL No. : | MFCD02179046 |
Formula : | C10H17NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ULMHMJAEGZPQRY-UHFFFAOYSA-N |
M.W : | 199.25 | Pubchem ID : | 7577838 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.79 |
TPSA : | 46.61 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) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 2.14 |
Log Po/w (XLOGP3) : | 1.31 |
Log Po/w (WLOGP) : | 1.55 |
Log Po/w (MLOGP) : | 1.16 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 1.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.7 |
Solubility : | 3.95 mg/ml ; 0.0198 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.89 |
Solubility : | 2.57 mg/ml ; 0.0129 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.4 |
Solubility : | 7.97 mg/ml ; 0.04 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
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 |
---|---|---|
91% | With dmap; triethylamine In dichloromethane at 20℃; for 3 h; | 395] To a solution of piperidin-2-one (0.97 g, 9.78 mmol) in DCM (20 mL) were added Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and B0C2O (3.20 g, 14.7 mmol). The reaction mixture was stirred at room temperature for 3 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/7) to give the title compound as pale yellow oil (1.78 g, 91percent). MS (ESI, pos. ion) m z: 144.2 [(M-C4)+H]+; 1H MR (600 MHz, CDCI3): δ (ppm) 3.65 (t, J= 6.1 Hz, 2H), 2.50 (t, J = 9.6, 7.2 Hz, 2H), 1.82 (m, 4H), 1.52 (s, 9H). |
91% | With dmap; triethylamine In dichloromethane at 20℃; for 3 h; | Step 1) fert-butyl 2-oxopiperidine-l-carboxylate [0359] To a solution of piperidin-2-one (0.97 g, 9.78 mmol) in DCM (20 mL) were added Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and B0C2O (3.20 g, 14.7 mmol). The reaction mixture was stirred at rt for 3 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/7) to give the title compound as pale yellow oil (1.78 g, 91percent). MS (ESI, pos. ion) m/z: 144.2 [(M-C4)+H]+; NMR (600 MHz, CDCb): δ (ppm) 3.65 (t, J= 6.1 Hz, 2H), 2.50 (t, J= 9.6, 7.2 Hz, 2H), 1.82 (m, 4H), 1.52 (s, 9H). |
91% | With dmap; triethylamine In dichloromethane at 20℃; for 3 h; | Piperidin-2-one (0.97 g, 9.78 mmol) was dissolved in DCM (20 mL) and then Et3N (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and Boc2O (3.20 g, 14.7 mmol) were sequentially added to the solution to obtain a reaction system. The resulting reaction mixture was stirred at room temperature for 3 hours, then concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (EtOAc / PE (v / v) = 1/7) to give the title compound as a pale yellow oil (1.78 g, 91percent). |
91% | With dmap; triethylamine In dichloromethane at 20℃; for 3 h; | Piperidin-2-one (0.97 g, 9.78 mmol) was dissolved in DCM (20 mL), and triethylamine (1.36 mL, 9.78 mmol), DMAP (0.12 g, 0.978 mmol) and Boc2O (3.20 g, 14.7 mmol) were added thereto and the resulting reaction mixture was stirred at room temperature for 3 hours and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc / PE (v / v) = 1/7) to give a pale yellow oil (1.78 g, 91percent). |
85% | With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48 h; | To a stirred solution of piperidin-2-one (5 g, 50.4 mmol, 1.0 equiv.), triethylamine (14.022 mL, 100.9 mmol, 2.0 equiv.) and N,N-4-dimethylaminopyridine (0.123 g, 1.0 mmol) in methylene chloride (100 mL) at 0° C. was added di-tert-butyl dicarbonate (16.512 g, 75.7 mmol, 1.5 equiv.). The mixture was slowly warmed to room temperature and stirred for 48 hrs. The reaction was quenched with water and the organic layer was washed sequentially with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column (0-100percent ethyl acetate/hexanes) to afford the desired product as a yellow oil (8.5 g, 85percent). 1H NMR (300 MHz, CDCl3): δ 3.72-3.62 (m, 2H), 2.58-2.48 (m, 2H), 1.90-1.78 (m, 4H), 1.55 (s, 9H). |
85% | With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48 h; | To a stirred solution ofpiperidin-2-one (5 g, 50.4 mmol, 1.0 equiv.),triethylamine (14.022 mL, 100.9 mmol, 2.0 equiv.)andN,N-4-dimethylaminopyridine (0.123 g, 1.0 mmol)in dichloromethane (100 mL)at 0 °Cwas addeddi-tert-butyl dicarbonate (16.512 g, 75.7 mmol, 1.5 equiv.).The mixture was slowly warmed to room temperature and stirred for 48 hrs. The reaction was quenched with water and the organic layer was washed sequentially with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonateand saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, filtered and concentratedin vacuo. The residue was purified by silica gel column (0-100percent ethyl acetate/hexanes) to afford the desired product as a yellow oil (8.5 g, 85percent).1H NMR (300 MHz, CDCl3): δ 3.72-3.62 (m, 2H), 2.58-2.48 (m, 2H), 1.90-1.78 (m, 4H), 1.55 (s, 9H). |
82% | With dmap In acetonitrile at 22℃; for 2 h; | In addition, this reaction can also be performed in a different reaction step. In a three necked round bottom flask fitted with: a stirring bar, a thermometer, and a bubler at 22° C., 1000 mg, (10 mmol) ö-Valerolactam was placed. Then a 0.7M solution of DMAP (60 g 0.4 mmol) in ACN (0.8 mE) was added. To the light-yellow solution (BOC)20 (3260 g 15 mmol) was portion wise added accompanied by gas evolution. After flall conversion (stirring at internal temperature 22° C. for 2 h) 10 mE 0.1M HC1 aq. solution were added and extracted with dichloromethane (3x20 mE). The organic phase was evaporated. Upon addition of 40 ml hexane and cooling to —30° C. and crystals where formed. Yield 82percent. Purity 98percent. The advantage of this reaction compared to the reaction mentioned above can be seen in that the reaction is performed at room temperature and that DMAP is easier to handle compared to BuEi. Furthermore,a higher degree of purity is achievable. |
77% | With dmap; triethylamine In acetonitrile at 0 - 20℃; for 18 h; | To a solution of 5.00 g (50.4 mmol, 1.0 eq.) 2-piperidinone in 250 mL acetonitrile, 8.44 mL (6.12 g,60.5 mmol, 1.2 eq.) triethylamine and 616 mg (5.04 mmol, 0.1 eq.) DMAP are added and the mixture iscooled to 0 °C. After slow addition of 12.7 mL (12.1 g, 55.4 mmol, 1.1 eq.) di-tert-butyl dicarbonate,the reaction mixture is stirred for 18 hours at ambient temperature. The solvent is removed and the crudeproduct is purified via column chromatography (SiO2, 6.5 10 cm, pentane/EtOAc = 5/1 3/1 1/1)to obtain 7.71 g (77 percent) tert-butyl-2-oxopiperidine-1-carboxylate as yellow oil. |
67.25% | With dmap; triethylamine In acetonitrile at 18℃; for 16 h; Inert atmosphere | 10300] To a solution of compound 1 (31.00 g, 312.72 mmol) in CH3CN (500 mE) was added TEA (63.29 g, 625.44 mmol), 13oc20 (88.73 g, 406.54 mmol), DMAP (1.91 g, 15.64 mmol) in portions under N2. The mixture was stirred at 18° C. for 16 hours. TLC showed the reaction was completed. The mixture was concentrated in reduced pressure at 35° C. The residue was purified by silica gel chromatography (PE/EA30/1 to 5/1) to afford compound 2 (41.90 g, 210.29 mmol, 67.25percent yield) as yellow oil. LCMS:200 [M+1]. |
6.07 g | With dmap In acetonitrile at 0℃; for 24 h; | In 250mL eggplant-shaped flask were successively added piperidin-2-one (5g, 50mmol), di- tert -butyl dicarbonate (13.1g, 60mmol), acetonitrile, 100mL, ice-cooling to 0 , was slowly added portionwise 4- dimethylaminopyridine (1.22g, 10mmol, plus complete,The reaction temperature 24h, TLC the reaction was complete, solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 15:1), to giveColorless oily liquid (6.07g, 30.5mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hydrogensulfate; N-ethyl-N,N-diisopropylamine In methanol | 4-Benzensulfonylmethyl-4-hydroxy-piperidine TFA (B-1) Diisopropylethylamine (28.3 mL, 162.75 mmol) and di-t-butyl dicarbonate (28.4 g, 130.02 mmol) were added in sequence to a mixture of piperidone hydrate hydrochloride (12) (10.0 g, 65.1 mmol) in methanol (50 mL). The mixture was stirred at room temperature for 20 hours. The solvent was removed, and the remaining was partitioned in ether and 1 M KHSO4 solution. The organic layer was washed with brine and saturated NaHCO3. The n-BuLi product was purified by flash chromatography to give a white solid (13) (12.0 g, 93percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 0.25 h; Stage #2: With mukaiyama’s reagent In tetrahydrofuran for 0.5 h; |
Diisopropylamine (1.7 mL, 12.1 mmol) of THF (10 mL)To the solution was added n-butyllithium (6.7 ml, 11.0 mmol) was added dropwise at -78 ° C., and the mixture was stirred for 30 minutes. Compound 34 (2 g, 10.0 mmol) in THF (10 mL) was added dropwise, and the mixture was stirred for 15 minutes. A solution of N-tert-butylbenzenesulfinimidoyl chloride (2.6 g, 12.1 mmol) in THF (5 mL) was added and the mixture was stirred for 30 minutes. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane / ethyl acetate) to give Compound 35 (750 mg, yield: 38percent) as an orange solid. |
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