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CAS No. : | 309956-78-3 | MDL No. : | MFCD03093382 |
Formula : | C10H20N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WUOQXNWMYLFAHT-MRVPVSSYSA-N |
M.W : | 200.28 | Pubchem ID : | 1514172 |
Synonyms : |
|
Chemical Name : | (R)-tert-Butyl piperidin-3-ylcarbamate |
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.9 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.3 |
TPSA : | 50.36 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) : | -6.78 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 1.05 |
Log Po/w (WLOGP) : | 0.88 |
Log Po/w (MLOGP) : | 0.86 |
Log Po/w (SILICOS-IT) : | 0.83 |
Consensus Log Po/w : | 1.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.48 |
Solubility : | 6.64 mg/ml ; 0.0332 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.7 |
Solubility : | 4.01 mg/ml ; 0.02 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.05 |
Solubility : | 1.8 mg/ml ; 0.00899 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.69 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
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 |
---|---|---|
95.4% | With palladium 10% on activated carbon; hydrogen In methanol; water at 35 - 40℃; for 2 h; Autoclave; Inert atmosphere | 46.8 g of compound IV, 2.3 g of 10percent wet palladium on carbon (water content 50percent) and 320 mL of methanol were added to the autoclave.Nitrogen replacement for 3 to 4 times, charging with hydrogen at a pressure of 0.3 to 0.4 MPa, raising the temperature to 35 to 40 ° C, and keeping the reaction for 2 h.The HPLC was traced to completion of the conversion of the starting material, filtered, concentrated to a fraction free, and 23 mL of dichloromethane and 46 mL of petroleum ether were added.Warm up to 35 ~ 40 ° C, slowly add 325 mL of petroleum ether at this temperature, keep warm for 1 h,Slowly cool down to -5 to 0 ° C, filter, and dry at 40 to 45 ° C to obtain 26.7 g of white (R)-3-Boc-aminopiperidine.The yield was 95.4percent. |
92% | With hydrogen In ethanol at 20℃; for 168 h; | (R) [PIPERIDIN-3-VL-CARBAMIC] acid [TERT.-BUTYL] ester (R) [3-TERT-BUTOXYCARBONYLAMINO-PIPERIDINE-1-CARBOXYLIC] acid benzyl ester (50 g, 150 [MMoL)] was dissolved in abs. [ETOH] (500 [ML),] and hydrogenated (1 atm, 7 days, 10 percent Pd/C (5.0 g) ) at RT. The reaction was filtered and evaporated in vacuo to give the product as a white solid. Yield 27.3 g [(92 percent).] 'H-NMR (dmso-d6,300 MHz) [6] [6.] 85 (d, [1 H),] 3.41 (s br, 2H), 3.05 (m, [1 H),] 2.90 (m, [1 H),] 2. [58-2.] 35 (m, 2H), 1.92 (m, 1 H), 1.75 (m, 1 H), 1.58 (s, 9H), 1.50-1. 40 (m, 2H). For analysis a small sample of the product (50 mg) was dissolved in EtOAc (2 [ML),] treated with 3 N HCI in EtOAc (2 [ML),] and evaporated in vacuo. The product was stirred with EtOAc (5 ml) for one hour and filtered to give (R) 3-aminopiperidine in > 98 percent ee, (determined as described in method G). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With palladium 10% on activated carbon; hydrogen In methanol at 45℃; for 2 h; | 2(R) -3-tert-butoxycarbonylamino-1-benzylpiperidine prepared in Example 4 was added, and thereto was added 10 g of a palladium Carbon (palladium content of the mass fraction of 10percent, moisture content of 53percent), installed after the kettle cover, hydrogen replacement system three times, to maintain the system pressure of about 1.5 atmospheric pressure, temperature 45 ° C, reaction 2 hours, with nitrogen replacement system three times, The filtrate was filtered through an appropriate amount of diatomaceous earth and the filtrate was spin dried to give (R) -3-tert-butoxycarbonylaminopiperidine, weighing 146 g, 85percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.7% | With sodium chloride; sodium hydroxide In water; butan-1-ol at 10 - 30℃; | A mixture was obtained by mixing 96. 5 g (0.274 mol, optical purity 97.4percent ee (R form)) of the diastereomer salt of t-butyl (R)-piperidin-3-ylcarbamate and,R-mandelic acid obtained in Example 31-2 with 12.5 g of sodium chloride, 97 ml of water, and 193 ml of 1-butanol. While maintaining the obtained mixture at 10 to 30°C, 115 g (0.287 mol) of an aqueous solution of 10 wtpercent sodium hydroxide was added thereto, and the resultant was stirred. An organic layer was obtained by a liquid-separation process. The water layer was extracted with 97 ml of 1-butanol, and the obtained organic layer and the organic layer previously obtained were mixed. The obtained organic layer was washed twice with 97 mL of water, and the obtained organic layer was concentrated under reduced pressure. To the concentration residue, 297 mL of 4-methyl-2-pentanone was added, and the obtained mixture was partially concentrated, whereby crystals were deposited. The crystals were collected by filtration and washed with 107 ml of ethyl acetate. By drying the obtained crystals, 43.7 g of t-butyl (R)-piperidin-3-ylcarbamate was obtained as a white crystal, with a yield of 79.7percent. The obtained t-butyl piperidin-3-ylcarbamate was derivatized with use of 3,5-dinitrobenzoyl chloride and analyzed by high-speed liquid chromatography, whereby the optical purity of the t-butyl piperidin-3-ylcarbamate was 99.8percent ee (R form).<optical purity analysis condition> column: CHIRALCEL AS-RH (4.6 * 150 mm, 5 μm)mobile phase: A = water, B = acetonitrile, A/B = 70/30flow rate: 1.0 ml/minutedetector: UV 254 nmholding time: S form = 10.4 minutes, R form = 15.6 minutes |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With formaldehyd; sodium cyanoborohydride In methanol; water at 20℃; | 163I. (R)-1-methylpiperidin-3-amine Sodium cyanoborohydride (4.51 g, 0.075 mol) was added in portion to a mixture of (R)-tert-butyl piperidin-3-ylcarbamate (10 g, 0.05 mol), 30percent water solution of formaldehyde (7.5 mL), and methanol (75 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and water. After extraction, the organic layers were washed with water, brine, and dried over Na2SO4. Concentration in vacuo, gave the N-methyl compound as an oil which was used directly without further purification. To a solution of the crude material previously obtained in methanol (60 mL) was added 4N HCl dioxane (10 mL). The reaction mixture was stirred at room temperature for 6 h. After concentration in vacuo, the residue was triturated with ether. The resulting precipitate was filtered and washed with ice-cold methanol to give the title compound as a solid (4.01 g, 72percent). 1H NMR (CD3OD, 400 MHz) δ 3.54 (1H, m), 2.81 (1H, m), 2.62 (1H, m), 2.23 (3H, s), 1.97 (1H, m), 1.67-1.87 (3H, m), 1.56-1.61 (1H, m), 1.41 (9H, s), 1.15-1.42 (1H, m). |
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