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CAS No. : | 1466-88-2 | MDL No. : | MFCD00007188 |
Formula : | C9H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VMSMELHEXDVEDE-HWKANZROSA-N |
M.W : | 177.16 | Pubchem ID : | 5367122 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In ethanol; at 20℃; for 16h;Inert atmosphere; | To a round bottom flask was charged with S11 (10.0 g, 0.056 mol, 1.0 equiv.), tert-butyl methylmalonate (12.3 ml, 0.074 mol, 1.3 equiv.), (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidi-ne (3.7 g, 0.011 mol, 0.2 equiv.), and 100 mL of EtOH. The reaction mixture was stirred atroom temperature for 16 h and was then concentrated in vacuo. Purification of the crudeproduct by flash chromatography on silica gel (petroleum ether:EtOAc, 5:1 v/v) afforded S2as a pair of diastereoisomers (15.1 g, 76percent), both as yellow oil.S2-upper: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.30; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.81 (d,J = 8.8 Hz, 1H), 7.55 (t, J = 7.2 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.39 (t, J = 8.4 Hz, 1H), 4.56 ? 4.50 (m, 1H),3.83 (d, J = 9.2 Hz, 1H), 3.57 (s, 3H), 3.12 ? 2.97 (m, 2H), 1.43 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 199.6,167.9, 166.5, 150.3, 134.8, 132.8, 129.3, 128.2, 124.7, 83.2, 57.2, 52.6, 46.6, 33.7, 27.8, 27.8, 27.8; IR (neat): vmax= 1727, 1355, 845, 749 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7, 374.1210; found 374.1210; [alpha]D25= +63.4 (c 0.20, MeOH).S2-lower: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.26; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.82 (d,J = 8.4 Hz, 1H), 7.55 (t, J = 8 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.38 (t, J = 7.6 Hz, 1H), 4.53 ? 4.47 (m, 1H), 3.87(d, J = 9.6 Hz, 1H), 3.73 (s, 3H), 3.08 ? 2.94 (m, 2H), 1.20 (s, 9H); 13C NMR (100MHz, CDCl3): delta 199.6, 168.4,165.9, 150.2, 135.0, 132.9, 129.5, 128.2, 124.7, 82.8, 57.1, 52.7, 47.3, 34.1, 27.4, 27.4, 27.4; IR (neat): vmax =1727, 1529, 844, 787 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7 374.1210; found 374.1210; [alpha]D25 =+32.5 (c 0.30, MeOH). | |
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In ethanol; at 20℃; for 16h; | Compound VII (10.0 g, 0.056 mol, 1.0 equiv.),Tert-butyl methyl malonate (12.3 ml, 0.074 mol, 1.3 equiv.)And (2S) -2- [diphenyl [(trimethylsilyl) oxy] methyl] -pyrrolidine VIII (3.7 g, 0.011 mol, 0.2 equiv.) was placed in a 250 mL round bottom flask,And add 100mL ethanol stirring.After 16h reaction at room temperature, the solvent was drained. Column chromatography (petroleum ether: ethyl acetate, 5: 1, v / v) gave two diastereomers IX-a and IX-b in 15.1 g total yield in 76percent yield. |
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