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CAS No. : | 30766-22-4 | MDL No. : | MFCD00191521 |
Formula : | C7H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KJJSHOHQQHACLE-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 354317 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
27% | With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 40℃; for 71h; | [0400] A suspension of (S)-3-Methanesulfonyloxy-piperidine-l-carboxylic acid tert-bupsilonXyl ester (2 g, 7.15 mmol), 5-hydroxynicotinic acid methyl ester (2.19 g, 14.32 mmol), and CS2CO3 (4.89 g, 15.03 mmol) in DMF (14 ml) is stirred at room temperature for 1 hour. The reaction is then heated to 40° C for 70 hours. After cooling to room temperature and concentration in vacuo, the reaction is dissolved in water (100 ml), extracted with EtOAc (50 ml), dried over MgSO4, filtered, and concentrated in vacuo. The residue is then purified by silica gel chromatography (10-50percent EtOAc/Hexanes) to provide (R)-methyl 5-(l-( tert- butoxycarbonyl)piperidin-3-yloxy)nicotinate (643 mg, 27percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃; for 24h;Inert atmosphere; | Triphenylphoshine (1052 mg, 4.01 mmol), 40% diethyl azodicarboxylatetoluene solution (698 mg, 4.01 mmol), and methyl 5-hydroxynicotinate(613 mg, 4.01 mmol) were added to a solution of 6(500 mg, 2.67 mmol) in tetrahydrofuran (18.0 mL) at 0 C under nitrogenatmospheric conditions. The resulting mixture was stirred for10 min and for an additional 24 h at room temperature and concentratedunder reduced pressure. The residue was purified by silica gelcolumn chromatography (petrolem ether/ethyl acetate=1/1) to yield7 (766 mg, 89%) in the form of a colorless oil: 1H NMR (300 MHz,CDCl3) δ: 8.83 (d, J=1.3 Hz, 1H), 8.51 (d, J=2.8 Hz, 1H), 7.81 (dd,J=2.8, 1.3 Hz 1H), 4.58-4.51 (m, 1H), 4.41-4.36 (m, 1H), 4.17 (dd,J=6.9, 2.9 Hz, 1H), 3.95 (s, 3H), 3.90 (t, J=7.5 Hz, 2H), 2.41-2.34(m, 1H), 2.31-2.26 (m, 1H), 1.42 (s, 9H); 13C NMR (75 MHz, CDCl3) δ:165.5, 155.9, 155.8, 142.9, 142.4, 126.3, 120.8, 79.5, 68.7, 59.8, 52.2, 46.9, 28.2 (3), 18.8; IR (CHCl3) cm-1: 3007, 2978, 2934, 1724, 1686,1589, 1394, 1367, 1302, 1151; FAB-MS m/z: 323.1611 (Calcd forC16H23N2O5: 323.1607); MS (FAB) m/z:323 (M++H, 62);[α]D20=-60.28 (c=1.01, CHCl3). |
88% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃;Inert atmosphere; | Under N2 stream, to a solution of 1 (0.50 g, 2.7 mmol) in THF(18 mL), triphenylphosphine (0.61 g, 4.0 mmol), diethyl azodicarboxylate (40% solution in toluene, 1.87 mL), and methyl 5-hydroxynicotinate(0.61 g, 4.0 mmol) at 0 C were added. The mixture was stirred at 0 C for 10 min and then warmed up to room temperature and stirred overnight. After the reaction, solvent was removed under reduced pressure, followed by silica gel chromatography (petroleume ther/ethyl acetate=1/1) to yield 2 (0.77 g, 2.4 mmol, 88%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ; 8.83 (d, J=1.3 Hz, 1H),8.51 (d, J=2.8 Hz, 1H), 7.81 (dd, J=2.8, 1.3 Hz, 1H), 4.58-4.51 (m,1H), 4.41-4.36 (m, 1H), 4.17 (dd, J=6.9, 2.9 Hz, 1H), 3.95 (s, 3H),3.90 (t, J=7.5 Hz, 2H), 2.41-2.34 (m, 1H), 2.31-2.26 (m, 1H), 1.42 (s,9H). 13C NMR (75 MHz, CDCl3) δ; 165.5,155.9, 155.8, 142.9, 142.4,126.3, 120.8, 79.5, 68.7, 59.8, 52.2, 46.9, 28.2, 18.8. MS (FAB+) m/z;323 ([M+H]+). HRMS (FAB+) m/z; 323.1611 (Calcd: 323.1607 for C16H23N2O5+). [α]D20= -60.28 (c=1.01, CHCl3). |
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