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CAS No. : | 2508-29-4 | MDL No. : | MFCD00008237 |
Formula : | C5H13NO | Boiling Point : | - |
Linear Structure Formula : | H2NCH2CH2CH2CH2CH2OH | InChI Key : | LQGKDMHENBFVRC-UHFFFAOYSA-N |
M.W : | 103.16 | Pubchem ID : | 75634 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P261-P280-P305+P351+P338-P310 | UN#: | 2735 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅲ |
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 trifluoromethylsulfonic anhydride; In dichloromethane; benzene; | A. 5-Phthalimido-1-pentyl triflate (15). To a solution of 5-aminopentanol (42.7 mmol) in benzene (100 mL) is added N-carbethoxyphthalimide (10.3 g, 47.0 mmol). The solution is stirred at room temperature for 5 h. The solvent is removed in vacuo to provide an oil, which is purified by flash chromatography. To a solution of 5-phthalimido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-phthalimido-1-pentyl triflate (15) which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoromethylsulfonic anhydride; acetic anhydride; triethylamine; In methanol; dichloromethane; | A. 5-Acetamido-1-pentyl triflate (30). A solution of 5-amino-1-pentanol (0.650 g, 6.31 mmol) in methanol (15 mL) is cooled to 0° C. and treated with triethylamine (1.62 mL, 11.6 mmol) followed by acetic anhydride (0.891 mL, 9.45 mmol). The reaction mixture is stirred at room temperature overnight. Additional triethylamine (1.6 mL, 11.6 mmol) and acetic anhydride (0.9 mL, 9.5 mmol) is added at room temperature and the solution is stirred 16 h further. Concentration in vacuo and flash chromatography affords 5-acetamido-1-pentanol. To a solution of 5-acetamido-1-pentanol (22.2 mmol) in dry dichloromethane (50 mL) is added <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (4.6 g, 22.2 mmol) and triflic anhydride (3.7 mL, 22.2 mmol) at 0° C. The reaction is stirred at room temperature for 20 min, poured into water, and extracted with dichloromethane. The combined extracts are dried over anhydrous sodium sulfate and concentrated in vacuo and to afford 5-acetamido-1-pentyl triflate (30) which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine; In dichloromethane; at 20℃; for 1.5h; | To a solution of 51 (430 mg, 1.48 mmol) in DCM (20 mL) was added a solution of 5-aminopentan-1-ol 55 (152 mg, 1.47 mmol) in DCM (4 mL) and Et3N (619 1iL, 449 mg,4.44 mmol). The mixture was stirred for 1.5 h at rt after which a saturated aqueoussolution of NaHCO3 was added (40 mL). After separation, the organic layer was dried (Na2SO4) and concentrated. The residue was purified by gradient column chromatography (EtOAc/heptane 1/1 -f 3/1). The product 56 was obtained as a colorless sticky liquid (356 mg, 1.27 mmol, 8 1%). ‘H NIVIR (400 IVIFIz, CDC13) (ppm) 4.68 (s,1H), 4.14 (d, J= 8.0 Hz, 2H), 3.65 (dd, J= 11.7, 6.3 Hz, 2H), 3.19 (dd, J 13.2, 6.7 Hz,2H), 2.35-2.15 (m, 6H), 1.66 - 1.30 (m, 7H), 1.02-0.88 (m, 2H). |