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CAS No. : | 129888-60-4 | MDL No. : | MFCD07787193 |
Formula : | C11H21NO5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WLAZHMYDLUILKR-UHFFFAOYSA-N |
M.W : | 279.35 | Pubchem ID : | 568122 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.91 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 71.45 |
TPSA : | 81.29 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.23 cm/s |
Log Po/w (iLOGP) : | 2.74 |
Log Po/w (XLOGP3) : | 1.09 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 0.93 |
Log Po/w (SILICOS-IT) : | 0.0 |
Consensus Log Po/w : | 1.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 3.29 mg/ml ; 0.0118 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.39 |
Solubility : | 1.14 mg/ml ; 0.00408 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.32 |
Solubility : | 13.2 mg/ml ; 0.0474 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.44 |
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 |
---|---|---|
100% | With triethylamine In dichloromethane at 0 - 20℃; for 3 h; | Step 1. methanesulfonyl chloride (3.130 g, 2.115 mL, 27.32 mmol) was added to a stirred solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (5 g, 24.84 mmol) and Et3N (5.027 g, 6.924 mL, 49.68 mmol) in DCM (50 mL) cooled to 0° C. on an ice-bath. The reaction was allowed to warm to ambient temperature over 3 hours. The reaction mixture was washed with water and 1M HCl, dried (MgSO4), filtered and concentrated in vacuo to give tert-butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate as a yellow oil (7.9 g, Quantitative yield-some residual solvent). 1H NMR (400.0 MHz, CDCL3) δ 1.49 (s, 9H), 1.60-1.57 (m, 1H), 2.04-1.79 (m, 3H), 3.08 (s, 3H), 3.38-3.32 (m, 1H), 3.50-3.43 (m, 1H), 3.70-3.60 (m, 2H) and 4.74 (br s, 1H) ppm; Step 2. |
100% | With triethylamine In dichloromethane at 0 - 20℃; for 2 h; | To a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (1.00 g, 4.97 mmol) in DCM (16 mL) was added TEA (0.895 mL, 6.46 mmol) followed by MsCl (0.465 mL, 5.96 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with DCM, washed with water, 2 N aq. HCl, saturated aq. NaHCO3, and brine successively, dried over Na2SO4, filtered and concentrated in vacuo to afford tert-butyl 3-(methylsulfonyloxy)piperidine-1-carboxylate (1.39 g, 100percent) as a colorless oil, which was used for the next reaction without further purification. 1H-NMR (CDCl3, Varian, 400 MHz): δ 1.47 (9H, s), 1.55 (1H, br. s), 1.78-2.01 (3H, m), 3.06 (3H, s), 3.28-3.38 (1H, m), 3.42-3.48 (1H, m), 3.54-3.68 (2H, m), 4.72 (1H, br. s). |
95.1% | at 0 - 20℃; | The solution of N-Boc-3-hydroxypiperidine (2.1 g, 10 mmol, 1.0 eq) and DIPEA (2.1 mL, 15 mmol, 1.5 eq) in 20 mL DCM was stirred. To the solution was slowly added dropwise methanesulfonyl chloride (1.0 mL, 13 mmol, 1.3 eq) after cooling to 0° C., and mixture was allowed to raise to room temperature. Then the reaction mixture was washed successively with a 1 M HCl solution, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution and water. The obtained DCM layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to give the product as a yellow solid (2.65 g, 95.1percent yield). MS m/z (ESI): 280.1 [M+H]. |
95% | With triethylamine In dichloromethane at 0 - 20℃; for 1 h; | Triethylamine (15 g, 150 mmol, 3.0 eq.) and methanesulfonyl chloride (6.3 g, 55 mmol, 1.1 eq.) were sequentially added dropwise to a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (10.0 g, 50 mmol, 1.0 eq.) in dichloromethane (100 mL) at 0° C. The reaction was stirred at 20° C. for 1 hour, quenched with saturated NaHCO3 (100 mL), and then extracted with methylene chloride (200 mL*3). The organic phase was dried over anhydrous sodium sulfate, and concentrated to give the title compound (13 g, yield: 95percent). |
93% | With triethylamine In dichloromethane at 0 - 20℃; for 3 h; | tert-Butyl 3-hydroxypiperidine-1-carboxylate (1.01 g, 4.97 mmol) , methylsufonyl chloride (0.77 mL, 9.94 mmol) and triethylamine (1.4 mL, 9.94 mmol) were mixed in DCM (15 mL) at 0 . The mixture was warmed to rt and stirred for 3 h. The reaction mixture was diluted with water (30 mL) . The resulting mixture was extracted with DCM (30 mL × 3) . The combined organic layers were washed with saturated aqueous NaCl (15 mL) , dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 3/1 to give a yellow liquid product (1.3 g, 93) .[1856]MS (ESI, pos. ion) m/z: 224.0 [M-t-Bu+2]+. |
85% | With dmap In dichloromethane at 0℃; for 2 h; | Hydroxypiperidine 20a (20.10 g, 0.1 mol) and DMAP (61.08 g, 0.5 mol) were co-evaporated with anhydrous dichloromethane (DCM) and suspended in 1 L DCM. The mixture was cooled to 0 °C and mesyl chloride (38 ml, 0.5 mol) was added dropwise under cooling and vigorous stirring. After 2 h TLC (10percent EtOH/CHCl3, ninhydrin detection) showed the complete consumption of the starting material. Water (20 ml) was added to the mixture and stirring continued for an additional 10 min. The mixture was extracted with saturated NaHCO3 (3.x.), and the combined organic phases were dried over anhydrous Na2SO4. Sodium sulfate was filtered off and the filtrate was evaporated. The product was purified by flash chromatography on a silica gel using a linear of gradient ethyl acetate in toluene. The product was obtained as a white amorphous solid in a 85percent yield (23.90 g, 85.5 mmol).νmax (KBr) 1693 (vs), 1463 (s), 1428 (s), 1245 (s), 1391 (m), 1365 (s), 1351 (vs), 1179 (vs), 976 (s), 938 (s), 929 (s), 904 (s), 543 (s), 524 (s); δH (DMSO, 499.8 MHz, 50 °C) 4.70 (1H, m, H-3), 3.60-3.64 (2H, m, H-2), 3.42 (1H, ddd, Jgem 13.4 Hz, J6b-5 7.2 and 3.9 Hz, H-6b), 3.34 (1H, ddd, Jgem 13.4 Hz, J6a-5 7.6 and 3.8 Hz, H-6a), 3.03 (3H, s, CH3SO2), 1.97 (1H, m, H-4b), 1.89 (1H, m, H-4a), 1.82 (1H, m, H-5b), 1.54 (1H, m, H-5a), 1.46 (9H, s, (C(CH3)3)); δC (CDCl3, 125.7 MHz, 50 °C) 154.7 (COO), 80.1 (C(CH3)3), 75.3 (C-3), 47.9 (C-2), 43.5 (C-6), 38.8 (SO2CH3), 30.5 (C-4), 28.3 (C(CH3)3), 21.7 (C-5); HRMS (FAB) C11H22NO5S (M+H)+ calcd 280.1212, found 280.1223. |
85% | With triethylamine In dichloromethane at 18℃; for 1 h; | To a mixture of compound 20-4-1A (200 g, 0.995 mol) and TEA (120.23 g, 1.19 mol) in DCM (700 mL), methylsufonyl chloride (125.24 g, 1.09 mol) was added in portions, and the reaction mixture was stirred at 18° C. for 1 h, followed by washed with water (1500 mL). The aqueous phase was extracted with DCM (500 mL×3), and then the organic phases were combined, dried over anhydrous Na2SO4, filtered and concentrated to give compound 20-4-1 (211 g, Yield 85percent) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 4.72 (s, 1H), 3.55-3.70 (m, 2H), 3.40-3.50 (m, 1H), 3.27-3.38 (m, 1H), 3.09-3.16 (m, 1H), 3.05 (s, 3H), 1.76-2.02 (m, 3H), 1.47 (s, 9H). |
77% | With triethylamine In tetrahydrofuran for 0.166667 h; Cooling | Stage (i): tert-Butyl 3-(methylsulfonyloxy)piperidine-1-carboxylate 1-Boc-3-hydroxypiperidine (0.5 g, 2.49 mmol) was dissolved in tetrahydrofuran (5 ml), triethylamine (0.75 g, 7.46 mmol) was added and the mixture was cooled. Methanesulfonic acid chloride (0.23 ml, 3 mmol) was added, the mixture was stirred in an ice bath for 10 min, saturated sodium bicarbonate solution (10 ml) was then added, as well as ethyl acetate (10 ml). Phase separation, the aqueous phase was extracted with ethyl acetate (2*20 ml) and the combined organic phases were washed with saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. Yield: 0.54 g (77percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dmap; triethylamine In tetrahydrofuran at 20℃; for 16 h; | Example 138Reagents and conditions: (a) NaH, DMF, 100 C, 16 h. (b) TFA, DCM, rt 1 h. (c) C8H7O2NCI2, HBTU, DIEA, THF, 50 C 16 h.[0567] Synthesis of tert-butyl 3-((methylsulfonyl)oxy)piperidine-l-carboxylate: To the solution of tert-butyl 3-hydroxypiperidine-l-carboxylate (2.01 g, 10 mmol, 1.0 eq) in THF (30 mL) was added DMAP (122 mg, 1.0 mmol, 0.1 eq), TEA (2.8 mL, 20 mmol, 2.0 eq) and methanesulfonic anhydride (1.91 g, 11 mmol, 1.1 eq). The mixture was stirred at rt for 16 h, filtered off and concentrated in vacuo to afford a residue which purified by column chromatography (silica gel, PE/EtOAc= 3: 1) to give the title product (2.5 g, yield: 90percent) as a colorless oil. 1H NMR (400 MHz, CDC13) δ: 4.72 (s, 1H), 3.74-3.61 (m, 3H), 3.45-3.42 (m, 1 H), 3.34-3.32 (m, 1H), 2.05-1.08 (m, 4H), 1.45-1.40 (m, 11H). ESI-MS (M+H+-56): 224.0. |
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