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CAS No. : | 137076-22-3 | MDL No. : | MFCD02179019 |
Formula : | C11H19NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JYUQEWCJWDGCRX-UHFFFAOYSA-N |
M.W : | 213.27 | Pubchem ID : | 1514430 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501 | 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 |
---|---|---|
In tetrahydrofuran; hexanes; at -78 - 20℃; for 0.5h; | To a suspension of methyltriphenylphosphonium bromide (1.76 g, 4.93 mmol) in THF (30 ml), cooled to -78 C., was added n-BuLi (1.88 ml of 2.5M soln. in hexanes; 4.68 mmol), and the mixture was stirred at -78 C. for 30 min and then at 0 C. for 45 min. It was cooled back to -78 C., and a solution of aldehyde 6 (0.50 g, 2.34 mmol) in THF (5 ml) was added. The reaction mixture was stirred at -78 C. for 30 min and warmed up to rt. It was quenched with water, and the product was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and purified by flash chromatography (0.5% MeOH/CH2Cl2) to provide 0.24 g of 20 as a clear oil. Step 2: BOC-deprotection and amide coupling steps as described in Example 2 were used to obtain the title compound MS (M+H): 347. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 17h; | Example 1; 4-[4-(4-Mcthancsulfonylphcnyl)pipcrazin-l -ylmcthyljpipcridinc-l -carboxylic acid tert-butyl ester; EPO <DP n="23"/>To a solution of l-(4-methanesulfonylphenyl)piperazine (0.41 mmol) and 4- formylpiperidine-1-carboxylic acid tert-mty ester (1.2 mmol) in DCM (3 mL) was added sodium triacetoxyborohydride (0.53 mmol). The resulting suspension was stirred at rt for 17 h. Polymer-supported isocyante scavenger resin (MP-NCO) (0.29 g, 1.44 mmol/g) was added and shaking continued until LCMS showed complete consumption of starting amine. The mixture was diluted with further DCM, shaken with water, and the organic layer separated using a hydrophobic frit. The crude mixture was purified via ion-exchange using an SCX column, to afford the title compound. deltaH (400 MHz, CHCl3) 1.14 (2H, m), 1.50 (9H, s), 1.70 (IH, m), 1.79 (2H, m), 2.26 (2H, d), 2.58 (4H, t), 2.74 (2H, m), 3.04 (3H, s), 3.38 (4H, t), 4.14 (2H, m), 6.96 (2H, d), 7.80 (2H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; In water; for 2h;Sonographic reaction; | A mixture of <strong>[30413-58-2]2-ethynyl-6-methyl-pyridine</strong> (0.08 g, 0.7 mmol), 1-Boc-4-piperidinecarboxaldehyde (0.1 g, 0.47 mmol), CuI (0.001 g, 0.11 mmol) and 33% w/w aqueous dimethylamine (0.077 mL, 0.56 mmol) in water (3 mL) was sonicated for 2 h in a laboratory ultrasonic bath. Afterwards, it was extracted with EtOAc and the combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to give a crude, which was purified by automated flash liquid chromatography (Horizon-Biotage) eluting with EtOAc-Petroleum Ether 1:1 affording the title product (0.11 g).1H-NMR (CDCl3, delta): 1.25-1.48 (m, 2H), 1.51 (s, 9H), 1.65-1.73 (m, 1H), 2.05-2.11 (m, 2H), 2.23-2.40 (br, 6H), 2.66 (s, 3H), 2.69-2.77 (m, 2H), 3.21-3.39 (m, 1H), 4.09-4.21 (m, 2H), 7.09-7.11 (m, 1H), 7.27-7.30 (m, 1H), 7.53-7.56 (m, 1H).MS: [M+H]+=358.6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of zinc trifluoromethanesulfonate (0.07 g, 0.19 mmol) and triethylamine (0.065 mL, 0.47 mmol) in anhydrous toluene (5 mL) was stirred at room temperature under nitrogen atmosphere. After 1 h, <strong>[30413-58-2]2-ethynyl-6-methyl-pyridine</strong> (0.13 g, 1.13 mmol) prepared as described in WO200544267 was added and after 15 min was dropped a solution of 1-Boc-4-piperidinecarboxaldehyde (0.2 g, 0.938 mmol) in toluene (1 mL): the resulting mixture was heated at 100 C. for 6 h. Afterwards, it was cooled to r.t., diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to give a crude, which was purified twice by automated flash liquid chromatography (Horizon-Biotage) eluting with CHCl3-MeOH 98-2 affording the title product (0.13 g) as a brown oil.1H-NMR (CDCl3, delta): 1.27-1.5 (m, 12H), 1.85-2.01 (m, 3H), 2.63 (s, 3H), 2.65-2.82 (m, 2H) 4.15-4.31 (m, 2H), 4.44-4.49 (m, 1H), 7.15-7.18 (m, 1H), 7.27-7.30 (m, 1H), 7.61-7.65 (m, 1H).MS: [M+H]+=331.6 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.7% | In tetrahydrofuran; at 0 - 20℃; for 1h; | To a stirred solution of t-butyl 4-formylpiperidine-1-carboxylate (0.5 g, 2.34 mmol) in THF (10 mL) was added MeMgBr (1.5M in THF) (3 mL, 4.68 mmol at 0 C. and reaction allowed to stir at room temperature for 1 h. Reaction was monitored by TLC. Reaction was quenched with aq. NH4Cl, extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to give 525 mg (97.7%) of t-butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate. MS: 230.2[M++1] |
Preparation 4; 4-(1-Methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester1: 4-(1-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl esterTo a solution of N-tert-butoxycarbonyl-4-piperidinecarboxaldehyde (32.20 g, 151.45 mmol) in tetrahydrofuran at -78 C. is added methyl magnesium bromide (2 M in diethyl ether, 100.96 mL, 302.89 mmol). The reaction is stirred at -78 C. for 4.5 h, and then warmed to -50 C. for 30 min. The reaction is quenched with water at -50 C. and allowed to warm to room temperature for 16 h. The solvents are removed and the material is partitioned between diethyl ether and 0.1 M hydrochloric acid. The mixture is extracted with diethyl ether. The combined organic layers are washed with 0.1 M hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated to dryness. The crude is purified by flash chromatography over silica gel to afford 16.90 g of the title compound as a colourless oil. MS (m/z) 229 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With perchloric acid; In water; at 0 - 20℃; | This example demonstrates a method for making compound 7-4R in Table 1. This example refers to the compound numbering in FIG. 1. (1S,2S,4R,6R,8S,9S, 11S,12S, 13R)-1 l-Hydroxy-8-(2-hydroxyacetyl)-9, 13- dimethyl-6-(piperidin- -yl)-5,7-dioxapentacyclo[10.8.0.002'9.04'8.01 '18]icosa-14,17-dien- 16-one (7-4R). [0527] To a solution of <strong>[638-94-8]desonide</strong> (1, 0.10 g, 0.25 mmol) in nitropropane (5 mL) was added aqueous perchloric acid (70%, 0.11 g, 0.75 mmol) dropwise at 0 C, followed by the addition of l-Boc- -piperidinecarboxaldehyde (4-4, 64 mg, 0.30 mmol). After being stirred at RT overnight, the suspension was concentrated in vacuo. The residue was basified by the addition of ammonia solution in methanol (7 M, 10 mL). The resulting mixture was concentrated in vacuo and the crude product was purified by prep-HPLC twice (method B) to yield compound 7-4R (15 mg, yield 13%) as a white solid. ESI m/z: 472 (M + H)+. MR (MeOD^, 500 MHz) delta 7 '.47 (d, J = 10.0 Hz, 1H), 6.27 (dd, J= 10.0 Hz, 2.0 Hz, 1H), 6.03 (s, 1H), 4.90 (d, J= 4.0 Hz, 1H), 4.50 (d, J = 19.0 Hz, 1H), 4.46-4.43 (m, 1H), 4.41 (d, J= 4.0 Hz, 1H), 4.29 (d, J= 19.0 Hz, 1H), 3.13-3.09 (m, 2H), 2.71-2.60 (m, 3H), 2.42-2.38 (m, 1H), 2.27-2.13 (m, 2H), 1.99-1.96 (m, 1H), 1.85-1.64 (m, 7H), 1.52 (s, 3H), 1.51-1.38 (m, 2H), 1.14-0.99 (m, 2H), 0.96 (s, 3H) ppm. The stereochemical R-configuration for compound 7-4R was determined by 2D NMR |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | General procedure: To a solution of cyclohexanecarboxyaldehyde 6a (0.224 mL, 1.85 mmol) in acetic acid (6 mL) phenylhydrazine (7) was added (0.182 mL, 1.85 mmol) and the reaction mixture was then heated to 80 °C for 2 h. Then methyl 4-formylbenzoate 8a (0.359 g, 1.85 mmol) in 1,2-DCE (6 mL) was added at 0 °C and after 15 min NaBH(OAc)3 (0.943 g, 4.25 mmol) was added portionwise. Reaction mixture was stirred at 25 °C for 12 h. Solvents were removed under reduced pressure, residue was diluted with 10 mL of EtOAc and washed with a saturated solution of Na2CO3. The combined organic phases were dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc/n-hexane 1:20) afforded the title compound as a yellow oil (yield 16percent). |
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