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Structure of 1032825-55-0

Chemical Structure| 1032825-55-0

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Product Details of [ 1032825-55-0 ]

CAS No. :1032825-55-0
Formula : C13H25NO5S
M.W : 307.41
SMILES Code : O=C(N1CCC(C(OS(=O)(C)=O)C)CC1)OC(C)(C)C

Safety of [ 1032825-55-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1032825-55-0 ]

* 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.

  • Downstream synthetic route of [ 1032825-55-0 ]

[ 1032825-55-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 183170-69-6 ]
  • [ 1032825-55-0 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; EXAMPLE 20 1-t-Butyloxycarbonyl-4-methanesulfonyloxyethylpiperidine Methanesulfonyl mL, was chloride (4.0 mL, 52 mmol) was added slowly to a 0 C. solution of <strong>[183170-69-6]1-t-butyloxycarbonyl-4-hydroxyethylpiperidine</strong> (10.0 g, 43.7 mmol) and diisopropylethylamine (7.3 mL, 52 mmol) in dichloromethane (100 mL) with stirring under a nitrogen atmosphere. After 24 hours at room temperature, the mixture was extracted with water (4*100 mL), dried (MgSO4), filtered, and concentrated in vacuo to yield a clear oil which crystallized upon standing. Mp:60-63 C. MSCI:252(MH+, base) 1 H NMR(300 MHz, CDCl3 /TMS, δ): 4.3(br t,2H), 4.1(br d,2H), 3.0(S,3H), 2.7(br t,2H), 1.7-1.1(m,16H).
  • 2
  • [ 183170-69-6 ]
  • [ 124-63-0 ]
  • [ 1032825-55-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0℃; for 0.5h; Step 4: tert-butyl 4-{l-[(methylsulfonyl)oxy]ethyl}piperidine-l-carboxylateTo a 250 ml round bottom flask was added tert-butyl 4-{ 1-[(methylsulfonyl)oxy] ethyl }piperidine-l-carboxylate from the previous step, triethylamine (27.4 ml, 196 mmol) and 100 ml methylene chloride. Methanesulfonyl chloride was added via a syringe at 0 0C. The resulting reaction mixture was stirred at 0 0C for 30 minutes. It was diluted with 300 ml ether, washed sequentially with 150 ml IN HCl, 100 ml saturated aqueous Na2CO3 and 100 ml brine. The organic layers were dried over sodium sulfate, filtered and concentrated to give 29 g light yellow sticky material.
With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; 2: 4-(1-Methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl esterTo a solution of <strong>[183170-69-6]4-(1-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester</strong> (18.24 g, 79.54 mmol) in dichloromethane (400 mL) and triethylamine (12.20 mL, 87.49 mmol) at 0 C. is added methanesulfonyl chloride (9.23 mL, 119.30 mmol). The reaction is allowed to warm to room temperature over 16 h. The mixture is washed with 0.1 M hydrochloric acid, saturated aqueous sodium bicarbonate, water, and brine. The material is dried over magnesium sulfate, filtered, and concentrated to dryness. The crude material is purified by flash chromatography over silica gel to afford 22.65 g of the title compound as a colourless oil. 1H NMR (CDCl3) δ (ppm): 1.19-1.30 (m, 2H), 1.39 (d, 3H), 1.44 (s, 9H), 1.6-1.8 (m, 3H), 2.66 (m, 2H), 2.99 (s, 3H), 4.16 (m, 2H), 4.62 (t, 1H).
815 g With triethylamine; In dichloromethane; at 0℃; for 0.5h; Compound 7 (655 g, 2.86 mol) was dissolved in dichloromethane (3.93 L)Triethylamine (598 mL, 4.29 mol) at room temperature,After the reaction system was cooled to 0 C,Methanesulfonyl chloride (392.6 g, 3.43 mol) was added dropwise,After completion of the dropwise addition,And the mixture was stirred at 0 C for 0.5 hour.The reaction solution was treated with HCl (1 N, 1.5 L)Water (2.0 L)And sodium carbonate (2 L)And brine (3 L)The organic phase was dried over anhydrous sodium sulfate,Filtered and concentrated to give compound 8 (815 g) as a yellow oil,Without further purification,Directly for the next reaction.
With triethylamine; In dichloromethane; at 0℃; for 2h; Intermediate 141, tert-butyl 4-(1 -hydroxyethyl)piperidine-1 -carboxylate (2.0 g, 8.73 mmol) andEt3N (3.64 mL, 26.3 mmol) were dissolved in dichloromethane (20.0 mL) and cooled to 0 C.Intermediate 142, methanesulfonyl chloride (0.82 mL, 10.4 mmol) was added dropwise andthe reaction mixture was allowed to stir at 0 C for 2 h. The reaction mixture was diluted withwater (100 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give crude tert-butyl 4-{1-[(methylsulfonyl)oxy]ethyl}piperidine-1-carboxylate (2.0 g, 75 %) as an oil. The crude product was used in the next step without further purification.LCMS (Method I): mlz 252 (M+H-56) (ES), at 4.51 mi UV active.
With triethylamine; In dichloromethane; at 0℃; for 4h;Inert atmosphere; To a solution of tert-butyl 4-(l-hydroxyethyl)piperidine-l-carboxylate (805 mg, 3.51 mmol) and triethylamine (0.979 mL, 3.86 mmol) in DCM (10 mL) was added mesyl-CI (0.301 mL, 3.86 mmol) at 0 C under an atmosphere of nitrogen. The reaction mixture was left to stir for 4 h. The reaction mixture was diluted with ether (30 mL) and washed sequentially with 1M aqueous HCI solution (20 mL), saturated aqueous NaHCC solution (20 mL) and brine (10 mL). The organic phase was passed through a hydrophobic frit and the solvent removed under reduced pressure to afford the crude title compound (980 mg). The material was used directly in the next step.

  • 3
  • [ 1032825-55-0 ]
  • [ 65417-22-3 ]
  • [ 1450658-79-3 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-aniline; at 120℃;Inert atmosphere; Cesium carbonate (844 g, 2.59 mol) was added to a solution of compound 4 (70 g, 0.37 mol) in N, N-dimethylaniline (700 mL)Under nitrogen compound will be heated to 120 .N, N-dimethylaniline (700 mL) of Compound 8 (170.6 g, 0.555 mol) was added dropwise to the reaction system,After completion of the dropwise addition,The reaction system was stirred at a constant temperature of 120 C until the raw materials reacted completely.The reaction was cooled to room temperature,Methyl tert-butyl ether (1.5 L) was added,After stirring for 10 minutes, filtration was performed.Water (2.5 L) was added to the filtrate,And methyl tert-butyl ether (1 L x 3).The organic phases were combined and washed with brine (2 L)Dried over anhydrous sodium sulfate,Concentration by filtration afforded crude compound 9 (630 g crude) as a yellow oil,Without further purification,Directly for the next reaction.
 

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