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2-(cyclobutylmethyl-amino)-cyclopentanecarboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With sodium acetate; sodium cyanoborohydride; In methanol; at 25℃; for 16h;4A molecular sieves;
2-Oxo-cyclopentanecarboxylic acid ethyl ester (0.24 mL, 1.64 mmol) and C-<strong>[848497-98-3]cyclobutyl-methylamine hydrochloride</strong> (0.20 g, 1.64 mmol) were dissolved in methanol (8 mL). Sodium acetate (0.27 g, 3.28 mmol) was added followed by 4A powdered molecular sieves (0.20 g) and sodium cyanoborohydride (0.21 g, 3.28 mmol). The reaction was stirred at 25 0C for 16 h. The mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution (20 mL) and ethyl acetate (30 mL). After shaking, both layers were passed through a plug of Celite. The <n="189"/>organic layer was further washed with saturated aqueous sodium bicarbonate solution (10 mL), saturated aqueous brine solution (10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, 2-(cyclobutylmethyl- amino)-cyclopentanecarboxylic acid ethyl ester (0.29 g, 1.30 mmol, 79%) as a clear oil. LC-MS (ESI) calcd for Ci3H23NO2 225.33, found 226.2 [M+H+].
5-(2-(2-bromo-3-chlorophenyl)hydrazono)-6-ethoxy-6-oxohexanoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; sodium acetate; sodium nitrite; In water; at 0 - 20℃; for 2.25h;
To a stirring mixture of <strong>[96558-73-5]2-bromo-3-chloroaniline</strong>(20 mmol) in 1M HCl(25 mL)and water(5 mL) at 0 oc was added NaN02(1.38 g,20 mmol) in water(20 mL),CH3C00Na(9.23 g,112 mmol) in water(25 mL) and ethyl 2-oxocyclopentane carboxylate(3.0 mL,20 mmol) in sequence. The reaction mixture was stirred for 15 min at 0 oc thenwarmed to 20 oc over 2h and extracted with CH2Ch,dried over MgS04,filtered and concentrated in vacuo to give the title compound as a red oil in 7.1 g(90% crude).
With hydrogenchloride; sodium acetate; sodium nitrite; In water; at 0℃; for 0.25h;
Step A. Preparation of 5-(2-(2-bromo-3-chlorophenyl)hydrazono)-6-ethoxy-6-oxohexanoic acid To a stirring mixture of <strong>[96558-73-5]2-bromo-3-chloroaniline</strong> (4.1 g, 20 mmol) in 1M HCl (25 mL) and water (5 mL) at 0 C. was added NaNO2 (1.38 g, 20 mmol) in water (20 mL), NaCH3COOH (9.23 g, 112 mmol) in water (25 mL) and ethyl 2-oxocyclopentane carboxylate (3.0 mL, 20 mmol) in sequence. The reaction mixture was stirred for 15 min at 0 C. then warmed to 20 C. over 2 h and extracted with CH2Cl2, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a red oil in 7.0 g (90% crude).
2-amino-6,7-dihydro-5H-cyclopenta[b]pyridine-3,4-dicarboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82.9%
To a solution of 74 mg of NaOEt in 1 mL of EtOH is added 180 mg of 3-amino-3-imino-propanoic ethyl ester hydrochloride at room temperature, followed by addition of 200 mg of 2-oxo- cyclopentanecarboxylic acid ethyl ester. The reaction mixture is heated to reflux for 2 h. A total of 860 mg of 20% NaCH aq. solution is added under reflux. The mixture is refluxed for another 1 h, and then cooled to room temperature. It is adjusted to pH = 5-6. The product is precipitated as solid. It is collected by filtration and washed with 1 mL of water twice. A total of 200 mg (yield 82.9%) of the desired product is obtained after being dried at 60C in vacuum oven. ?H NMR (400 MHz, D20 with NaCD): 8 2.68 (t, 2H), 2.61 (t, 2H), 1.95 (m, 2H); ?3C NMR (100 MHz, D20 with NaOD): 8 176.77, 173.75, 165.36, 157.06, 147.52, 122.96, 110.19, 33.51, 28.31, 22.42; MS (m/z+1): 223.1.
ethyl 1-(6-fluoro-3-(p-tolyl)-1H-isochromen-1-yl)-2-oxocyclopentanecarboxylate[ No CAS ]
C24H23FO4[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With diphenyl hydrogen phosphate; silver carbonate; In hexane; at 40℃; for 36.0h;
General procedure: A dry single-necked flask was charged with 2-alkynylaldehyde 1 (0.4 mmol, 1 equiv), ketone 2 (0.8 mmol, 2 equiv), and diphenylphosphate (10 mg, 0.04 mmol, 10 mol %) in hexane (2.4 mL), and silver carbonate (2.75 mg 0.01 mmol, 2.5 mol%) was added. The mixture was heated to 40 C and stirred until the 2-alkynylaldehyde was completely consumed (progress of the reaction was monitored by TLC). The hexane was evaporated and the mixture was diluted in EtOAc (50 mL) and washed three times with water. The organic layer was dried over anhydrous Na2SO4 and filtered. After evaporating the EtOAc, the crude product was dissolved in dichloromethane and purified by column chromatography (silica gel; pentane/EtOAc, 96:4) to give pure 1H-isochromenes 3 as yellow oils or as colorless solids. In the case of phenylacetone and 2-phenylcyclohexanone as ketone nucleophiles, the crude product was directly purified by flash chromatography on silica gel.
5-((2-bromo-3-chlorophenyl)diazenyl)-6-ethoxy-6-oxohexaneoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a stirred solution of <strong>[96558-73-5]2-bromo-3-chloro-aniline</strong> (CAS 96558-73-5, 50 g, 242 mmol) in aqueous hydrochloric acid (2.5 M, 500 ml_) was added sodium nitrite (17 g, 247 mmol) in water (100 ml_) drop-wise at 0 O over 0.5 hour. After add ition, the mixture was stirred at 0 for 0.5 hour. Then sodium acetate (84 g, 1.02 mol) in water (500 ml_) was added into the reaction mixture, followed by ethyl 2-oxocyclopentanecarboxylate (40 g, 256 mmol). The mixture was stirred at 0 6 for 0.5 hour and then it was warmed to 25 O and stirred for 1 hour. Dichloromethane (800 ml_) was added into the reaction mixture. Two layers were separated and the aqueous layer was extracted with dichloromethane (300 ml_ x 3). The combined organic layer was washed with water (300 ml_ x 3), dried over sodium sulfate, filtered and concentrated by evaporation in vacuum to give 5-((2-bromo-3-chlorophenyl)diazenyl)-6-ethoxy- 6-oxohexanoic acid (108 g, crude) as black oil, which was used directly for the next step.
To a stirred solution of <strong>[96558-73-5]2-bromo-3-chloro-aniline</strong> (CAS 96558-73-5, 50 g, 242 mmol) in aqueous hydrochloric acid (2.5 M, 500 ml_) was added sodium nitrite (17 g, 247 mmol) in water (100 ml_) drop-wise at 0 over 0.5 hour. After add ition, the mixture was stirred at 0 for 0.5 hour. Then sodium acetate (84 g, 1.02 mol) in water (500 ml_) was added into the reaction mixture, followed by ethyl 2-oxocyclopentanecarboxylate (40 g, 256 mmol). The mixture was stirred at 0 6 for 0.5 hour and then it was warmed to 25 and stirred for 1 hour. Dichloromethane (800 ml_) was added into the reaction mixture. Two layers were separated and the aqueous layer was extracted with dichloromethane (300 ml_ x 3). The combined organic layer was washed with water (300 ml_ x 3), dried over sodium sulfate, filtered and concentrated by evaporation in vacuum to give 5-((2-bromo-3-chlorophenyl)diazenyl)-6-ethoxy- 6-oxohexaneoic acid (108 g, crude) as black oil, which was used directly for the next step.
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