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CAS No. : | 5570-78-5 | MDL No. : | MFCD00101977 |
Formula : | C8H17NO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | UZRXHHMTKCJKTQ-UHFFFAOYSA-N |
M.W : | 143.23 | Pubchem ID : | 79681 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
43% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃; for 0.5h; | To a cold (0 C.) mixture of <strong>[24985-85-1]5-hydroxy-1H-indole-2-carboxylic acid ethyl ester</strong> (10 g, 1.0 eq.), 1-isopropyl-piperidin-4-ol (intermediate 1, step 1, 7.32 g, 1.05 eq.) and triphenylphosphine (15.3 g, 1.2 eq.) in tetrahydrofuran (280 ml) was slowly added a solution of diisopropylazodicarboxylate (11.8 g, 1.2 eq.) in tetrahydrofuran (20 mL). The mixture was stirred 30 min at 0 C. and overnight at room temperature, was concentrated in vacuo, dissolved in methyltertiobutylether (310 mL), washed with sodium hydroxide aqueous solution (0.5N), brine, dried over Na2SO4, filtered and evaporated. The residue was purified on silica eluding with dichloromethane/methanol/ammoniac. One fraction was isolated and dried in vacuo, to yield 7.0 g (43%) of the desired product as white solid. MS (m/e): 331.5 (MH+, 100%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 48h; | To a cold (0 C.) solution of <strong>[24985-85-1]5-hydroxyindole-2-carboxylic acid ethyl ester</strong> (purchased at Biosynth, ref H-6350, 20 g, 1.0 eq.), 1-isopropylpiperidin-4-ol (intermediate 1, step 1, 16.75 g, 1.2 eq.) and triphenylphosphine (30.68 g, 1.2 eq.) in tetrahydrofuran (500 mL) was slowly added a solution of di-tert-butylazodicarboxylate (26.93 g, 1.2 eq.) in tetrahydrofuran (100 mL). The reaction mixture was stirred at room temperature for 48 h then evaporated to dryness in vacuo and purified on silica, eluding with a gradient of solvent from dichloromethane/ethyl acetate 19:1 to dichloromethane/methanol/ammonium hydroxide 95:5:0.25. One fraction was isolated and dried in vacuo, to yield 21.53 g (66%) of the desired product as white solid. MS (m/e): 331.1 (MH+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 16h; | General procedure: A solution of methyl 4-hydroxybenzoate derivatives 4a-4f (1 mmol), 1-substituted-4-piperidinol I-IV (1.3 mmol) and triphenylphosphine (1.5 mmol) in tetrahydrofuran (90 mL) was treated with diethyl azodicarboxylate (1.5 mmol) dropwise at 0 °C. The mixture was left at 0 °C for 15 min and stirred overnight at room temperature. After completion of the reaction, the reaction mixture was poured onto cold water, the resulting solution was extracted with dichloromethane, washed with brine, dried over Na2SO4, concentrated in vacuo and purified by flash chromatography. Thus the reaction of 4a-4f with various I, II, III and IV gave intermediates 5a-5i. |
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