Purity | Size | Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity |
95% | 250mg | $274.00 | Inquiry | Inquiry | |
95% | 1g | $685.00 | Inquiry | Inquiry |
CAS No. : | 120686-00-2 | MDL No. : | MFCD26406741 |
Formula : | C12H13NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPTRBDFGSOAYQF-UHFFFAOYSA-N |
M.W : | 235.24 | Pubchem ID : | 54696199 |
Synonyms : |
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 |
---|---|---|
With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h; | General procedure: To a solution of beta-ketoester 10a (1 mmol), 1,1,3,3-tetramethylguanidine (26 muL, 0.2 mmol) in dichloromethane (2.5 mL) was added alpha,beta-unsaturated aldehyde 11a (10 mmol). The reaction mixture was stirred at room temperature for 12 h and then the solvent was removed under vacuum. The residue was purified by silica gel chromatography to yield the bridged product 12a. To a solution of the alcohol 12a (0.5 mmol) and trimethylamine (690 muL, 5 mmol) in 2.5 mL of dichloromethane was added dropwise mesyl chloride (154 muL, 2 mmol) and a catalytic amount of DMAP at room temperature. The solution was stirred for 12 h at room temperature, and then diluted with dichloromethane, washed with satd aq NH4Cl, dried and concentrated. The above crude product was dissolved in HOAc (10 mL), and NaOAc (48 mg, 0.6 mmol) was added. The solution was heated to reflux for 24 h. After concentration in vacuum, the residue was treated with satd aq NaHCO3, and extracted with ethyl acetate. The combined organic extracts was washed with brine and dried. After concentration in vacuum, the residue was purified by silica gel chromatography to give rac-13a. | |
With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h; | rac-4 To a solution of beta-keto ester 2 (0.5 mmol),1,1,3,3-tetramethyl guanidine (13 mL, 0.1 mmol) in dryDCM (2 mL) was added methacrolein 3 (5 mmol). Thereaction mixture was stirred at room temperature for 12 hand then the solvent was removed under vacuum. Theresidue was purified by silica gel chromatography to yieldthe rac-9. To a solution of the alcohol rac-9 (0.25 mmol)and triethylamine (340 muL, 2.5 mmol) in 2 mL of DCMwas added dropwise mesyl chloride (77 muL, 1 mmol) and DMAP (3 mg, 0.025 mmol) at room temperature. Thesolution was stirred for 12 h at room temperature, andthen diluted with DCM, washed with saturated aq NH4Cl,dried and concentrated. The above crude product was dissolvedin HOAc (5 mL), and NaOAc (24 mg, 0.3 mmol)was added. The solution was heated to reflux for 24 h.After concentration in vacuum, the residue was dissolvedin ethyl acetate, was washed with saturated Na2CO3 andbrine, dried over Na2SO4. Evaporation of the ethyl acetateand flash chromatography of the residue (20 % and then40 % ethyl acetate in hexanes) gave 79 mg of rac-4 in 55 %yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; at 85 - 90℃; for 2h;Inert atmosphere; | Sodium hydride (50%, 27.7 g, 1.2 equivalents) and dimethyl carbonate (1,275 ml) were heated to 85-90 C. under nitrogen atmosphere, and the ketone of Formula (4) (85 g, 1.0 equivalent) diluted with dimethyl carbonate (1,275 ml) was added drop wise over a period of 1.5 hours. After addition, the reaction mixture was maintained at the same temperature for approximately 30 minutes. A sample for HPLC showed <1% of the ketone starting material remained. Dimethyl carbonate was then distilled off completely under vacuum at 40-45 C., and the residue was cooled to 10-15 C. Chilled water was added and dissolved completely. The pH was adjusted to 2-3 by adding 5 N HCl (160 ml) and extraction was performed with ethyl acetate (1 time with 340 ml and 2 times with 170 ml). The solvent was distilled off completely to get the crude beta-keto ester of Formula (5). The crude ester was dissolved in 800 ml 5% ethyl acetate:hexane mixture by heating at 60-65 C. The resulting mixture was allowed to cool to ambient temperature (20-25 C.) and filtered through filter paper. The solvent was distilled off completely under vacuum at 40-45 C. The resulting residue was stirred with hexane for 30 minutes at 20-25 C. The product was then collected by filtration and bed washed with portions of hexane. The product was dried under vacuum (740-750 mm/Hg) at 25-30 C. for 2 hours to yield pure product (80.2 g, 71% yield, HPLC purity-98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a suspension of (2R)-catalyst 8b(18 mg, 0.03 mmol) and benzoic acid (12 mg, 0.1 mmol)and the beta-keto ester 2 (47 mg, 0.2 mmol) in dry DCM(2 mL) was added methacrolein 3 (84 mg, 1.2 mmol) at0 C. The reaction mixture was refluxed for 4 days, then thesolvent was removed under vacuum, the residue was dissolvedin DCM (2 mL), and then DBU (42 muL, 0.3 mmol)was added. The reaction mixture was stirred at room temperaturefor 2 h, and the solvent was removed under vacuum,then ethyl acetate and saturated NaCl were added. Theorganic phase was separated and the aqueous phase wasextracted with ethyl acetate. The combined organic layerswere dried over Na2SO4 and concentrated to give the crudeproduct. Purification of the residue by flash column chromatography(silica gel) eluting with 20 % ethyl acetate in hexanesgave 50 mg of 9 (82 %) as a mixture of diastereomers.1H NMR (400 MHz, CDCl3) (main diastereomer): delta 7.07 (d,J = 8.8 Hz, 1H), 6.62 (d, J = 8.4 Hz, 1H), 3.89 (s, 3 H),3.73 (s, 3 H), 3.70-3.78 (m, 1H), 3.43 (dd, J = 5.2, 17.6 Hz,1H), 3.43 (dd, J = 2.0, 18.0 Hz, 1H), 3.17 (dd, J = 6.8,13.2 Hz, 1H), 2.77-2.80 (m, 1H), 2.18 (brs, 1H), 1.71-1.78(m, 1H), 1.61-1.66 (m, 1H), 0.88 (d, J = 6.8 Hz, 3H); 13CNMR (100 Hz, CDCl3): delta 207.01, 171.77, 163.26, 149.88,138.74, 128.39, 110.45, 80.28, 60.28, 54.66, 53.70, 53.01,41.85, 39.20, 34.56, 17.58; ESI-MS m/z: 306.1 [M + H]+;ESI-HRMS calcd for C16H20NO5+ [M + H]+ 306.1339,found 306.1336 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | A chiral ligand according to Formula (13) (2.13 g, 2 mol %), allyl palladiumchloride dimer (0.56 g, 1 mol %), and acetone (140 ml) were combined and stirred at 20-25 C. for 1 hour under a nitrogen atmosphere. To the mixture was added 2-methylene-1,3-propanediol diacetate (26.2 ml, 1.0 equivalent) and 35 ml of acetone and the new mixture was maintained at the same temperature for 1 hour. A mixture of the purified keto ester of Formula (5) (35 g, 1.0 equivalent), 1,1,3,3-tetramethyl guanidine (42 ml, 2.2 equivalents), and acetone (175 ml) was added to the above solution in lots over a period of 30 minutes at 20-25 C. The resulting mixture was then stirred at the same temperature for 1 hour under a nitrogen atmosphere. A sample for chiral HPLC indicated <1% starting material (keto ester) remained. Acetone was then distilled off under vacuum at 40-45 C. to obtain a crude material. The Crude material was passed through silica gel column and eluted with hexane and ethyl acetate mixtures to remove catalyst and ligand. The fractions containing product were collected and the solvent was distilled completely to yield pure product of the compound of Formula (6) (35 g, 82% yield, HPLC purity of 78%). This crude product (35 g) was stirred with isopropyl alcohol (140 ml) at 20-25 C. for 30 minutes. The obtained solid was filtered and washed with isopropyl alcohol (17.5 ml), and the material was dried under vacuum for 2-3 hours at 35-40 C. to get pure product as a white solid (21 g, 50% yield, HPLC purity of 97.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h; | General procedure: To a solution of beta-ketoester 10a (1 mmol), 1,1,3,3-tetramethylguanidine (26 muL, 0.2 mmol) in dichloromethane (2.5 mL) was added alpha,beta-unsaturated aldehyde 11a (10 mmol). The reaction mixture was stirred at room temperature for 12 h and then the solvent was removed under vacuum. The residue was purified by silica gel chromatography to yield the bridged product 12a. To a solution of the alcohol 12a (0.5 mmol) and trimethylamine (690 muL, 5 mmol) in 2.5 mL of dichloromethane was added dropwise mesyl chloride (154 muL, 2 mmol) and a catalytic amount of DMAP at room temperature. The solution was stirred for 12 h at room temperature, and then diluted with dichloromethane, washed with satd aq NH4Cl, dried and concentrated. The above crude product was dissolved in HOAc (10 mL), and NaOAc (48 mg, 0.6 mmol) was added. The solution was heated to reflux for 24 h. After concentration in vacuum, the residue was treated with satd aq NaHCO3, and extracted with ethyl acetate. The combined organic extracts was washed with brine and dried. After concentration in vacuum, the residue was purified by silica gel chromatography to give rac-13a. |
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