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With ammonium acetate In butan-1-ol for 3 h; Reflux
A mixture of 4-oxo-piperidine- 1 -carboxylic acid tert-butyl ester (3.5 g, 17.55 mmol) (Sigma- Aldrich), malonic acid (2.0 g, 19.30 mmol) and ammonium acetate (3.1 g, 40.36 mmol) in n-BuOH was refluxed for 3 h. After cooled, white solid was collected, rinsed with EtOAc and dried in vacuo to provide the title compound 1.61 g (6.2 mmol) in 36percent yield. NMR (200 MHz) in D20, δ ppm: 3.66 (br m, 2 H), 3.10 (br m, 2H), 2.45 (s, 2 H), 1.69 (br m, 4 H), 1.28 (s, 9 H).
With ammonium acetate; In butan-1-ol; for 3.0h;Reflux;
A mixture of 4-oxo-piperidine- 1 -carboxylic acid tert-butyl ester (3.5 g, 17.55 mmol) (Sigma- Aldrich), malonic acid (2.0 g, 19.30 mmol) and ammonium acetate (3.1 g, 40.36 mmol) in n-BuOH was refluxed for 3 h. After cooled, white solid was collected, rinsed with EtOAc and dried in vacuo to provide the title compound 1.61 g (6.2 mmol) in 36% yield. NMR (200 MHz) in D20, delta ppm: 3.66 (br m, 2 H), 3.10 (br m, 2H), 2.45 (s, 2 H), 1.69 (br m, 4 H), 1.28 (s, 9 H).
A 20-mL scintillation vial was charged with l-cyano-4-hydroxy-7-phenoxy-isoquinoline-3- carboxylic acid methyl ester (100 mg, 0.31 mmol), 4-amino-4-carboxymethyl-piperidine- 1 -carboxylic acid tert-butyl ester (322 mg, 1.25 mmol), NaOMe (59 mg, 1.09 mmol) and dimethylacetamide (3 mL). It was close-capped and heated in a 150 C oil bath for 4 h. Reaction mixture was diluted with water (70 mL) and acidified by 1 N HC1 to pH = 4-5. Precipitate was collected, rinsed with water and dried. Crude product was purified by silica gel chromatography, eluting with 10- 100% EtOAc / hexanes, to provide the title compound 92 mg (0.16 mmol) in 54 % yield. LC-MS ESI-: 545.08 (M- l)~ .
beta3,3Pip(Boc)-OH (5.0mmol,1.290g) was dissolved in 1.0ml ofpyridine followed by the addition of acetic anhydride (7.0mmol ,0.80ml) andstirred the reaction for 5hr.Thereaction was monitored by TLC, then quench the reaction with saturated Na2CO3 solution, followed by acidification and was extracted with EtOAc (3×15 ml) and brinesolution. The organic layer was dried over anhydrous sodium sulphate andevaporated in vacuo, The residue was filtered through a sintered funnel and waswashed with ethyl acetate to give the desired compound Ac- beta3,3Pip(Boc)-OH,1.Which was used further withoutpurification.
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