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CAS No. : | 156185-63-6 | MDL No. : | MFCD02677712 |
Formula : | C13H25NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OXPWHPCCUXESFQ-UHFFFAOYSA-N |
M.W : | 243.34 | Pubchem ID : | 2800739 |
Synonyms : |
|
Chemical Name : | tert-Butyl 4-(3-hydroxypropyl)piperidine-1-carboxylate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
With sodium hydroxide; potassium hydrogensulfate; In 1,4-dioxane; | b 3-[N-(tert-butoxycarbonyl)piperidin-4-yl]propanol A solution of 6 g of di(tert-butyl)carbonate in 20 ml of dioxan was introduced into a solution of 3.2 g of 3-(4-piperidinyl)propanol in 50 ml of dioxan containing 25 ml of a 2N aqueous solution of sodium hydroxide, cooled at 0° C. The mixture was allowed to react for 16 hours at room temperature. The solution was then evaporated and the residue was extracted with ethylether. The organic layer was washed with a 10percent solution of KHSO4 and then dried over MgSO4. The solvent was evaporated and the residue was chromatographied on silica gel (eluent: CH3 COOEt/cyclohexane:2/8-1/1:v:v). 3 g of the desired compound in the form of an oil were obtained. RMN (CDCl3, 200 MHz) 4.05 ppm (m, 2H); 3.6 (t, 2H); 2.64 (m,2H); 1.7 a 1.1 (m, 18H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In dichloromethane; at 20℃; for 2h; | Preparation 144-(3-Aminopropyl)-piperidine-1-carboxylic acid tert-butyl ester(A). Preparation of 4-(3-hydroxypropyl)-piperidine-1-carboxylic acid tert-butyl ester; Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) is added to a stirred solution of 3-piperidin-4-yl-propan-1-ol (1.60 g, 11.2 mmol) in anhydrous dichloromethane (20 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir for 2 hours. The mixture is directly subjected to chromatography purification on silica gel and eluted with MeOH in dichloromethane 0-3percent to give the title compound as a clear oil (2.40 g, 88percent yield). |
82% | In ethanol; | 1) Synthesis of 3-(1-tert-butoxycarbonyl-4-piperidyl)-1-propanol To a solution of 35.8 g (250 mM) of <strong>[7037-49-2]3-(4-piperidyl)-1-propanol</strong> in 500 ml of ethanol was added 54.6 g (250 mM) of di-tert-butyl dicarbonate dropwise and the mixture was stirred at room temperature for one hour. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography (ethyl acetate-hexane=1/1 ethyl acetate) to provide the title compound as light-yellow oil (50.2 g, 82percent). 1H-NMR (200 MHz, CDCl3) delta: 0.96-1.41 (m, 5H), 1.45 (s, 9H), 1.49-1.78 (m, 4H), 2.61-2.74 (m, 2H), 3.62 (t, J=6.4 Hz, 2H), 4.04-4.10 (m, 2H). |
With sodium hydroxide; In 1,4-dioxane; at 0 - 20℃; for 12h; | To a solution of 3- (piperidin-4-yl) propan-1-ol (8.1 g, 56.7 mmol) and 3M NaOH (100 mL) in dioxane (300 mL) was added a solution of Boc2O (15.0 g, 68.0 mmol) in dioxane (30 mL) dropwise at 0. After stirring at rt for 12 h, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc (600 mL) . The organic phase was washed with sat. NH4Cl (30 mL) , NaHCO3 (30 mL) and brine (30 mL) , dried over anhydrous Na2SO4, filtered and concentrated to afford tert-butyl 4- (3-hydroxypropyl) piperidine-1-carboxylateas which was used in next step without purification. LRMS m/z (M-55) 188.1 found, 188.2 required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 2h; | The solution of tert-butyl 4- (3-hydroxypropyl) piperidine-1-carboxylate (5 g, 20.6 mmol) in 2M HCl/1, 4-dioxane (20 mL) was stirred for 2 h at rt. Then the mixture was concentrated in vacuo to give crude 3- (piperidin-4-yl) propan-1-ol. LRMS m/z (M+H) 144.0 found, 144.1 required |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.5 g | With diisobutylaluminium hydride; In dichloromethane; at -78 - 0℃; for 2h;Inert atmosphere; | In a 500-ml flask swept with nitrogen, 5 g (17.53 mmol) of <strong>[162504-75-8]tert-butyl 4-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate</strong> (prepared according to the method reported in J. Med. Chem. 1995, 38, p 3332-3341 by taking commercial tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate as the starting product) in 100 ml of dichloromethane. The medium is cooled to -78 C. and 52.6 ml (52.6 mmol) of a 1 M solution of DIBAL-H in dichloromethane are added dropwise. It is stirred for 2 h at 0 C. It is cooled to -78 C. and a saturated solution of potassium sodium tartrate is added. After return to room temperature, it is extracted and then the organic phase is dried on Na2SO4, filtered and evaporated, and 4.5 g of the crude oil are obtained, used as is in the next step. |
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