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CAS No. : | 332-77-4 | MDL No. : | MFCD00003220 |
Formula : | C6H10O3 | Boiling Point : | - |
Linear Structure Formula : | C4H4O(OCH3)2 | InChI Key : | WXFWXFIWDGJRSC-UHFFFAOYSA-N |
M.W : | 130.14 | Pubchem ID : | 78974 |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | 1993 |
Hazard Statements: | H225-H302-H315-H319-H335 | 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 sodium acetate; In methanol; water; for 48.0h;pH 4.5 - 4.9; | To a 3 L flask with 53.6 g (0.41 mol) of 2,5-dimethoxydihydrofuran was added 1000 ml of 3N HCl solution.. The mixture was left to stand for 12 h at room temperature and then neutralized with ice-cold NaOH solution (equal moles) at 0 C. To this red solution, was added 41.3 g (0.62 mol) of methylamine hydrochloride in 300 ml H2O, the preformed methanol solution of the monomethylester (50 g (0.39 mol) of acetone dicarboxylic acid anhydride in 160 ml of methanol) and 50 g of sodium acetate in 200 ML of H2O. The mixture (PH 4.5) was stirred for 2 days and the acidity decreased to PH 4.9.. The red solution was extracted with hexane (450 ml*2) to remove nonpolar by-products.. The aqueous solution was basified first with NaOH (1N) to neutral PH, then with potassium carbonate.. sodium chloride (about 200 g) was added.. The saturated solution was extracted with CH2Cl2 (250 ml*8), then with a mixed solvent (t-butyl:1,2-dichloroethane, 37:63, 250 ml*8).. The CH2Cl2 extracted was dried over K2CO3 and solvent was removed to provide 19.6 g of a crude mixture which was separated by column chromatography (SiO2, 10% Et3N, 30-90% EtOAc in hexane and 10% methanol in EtOAc) to afford 7.5 g of 6(7)-methoxy-2-methoxycarbonyl-8-azabicyclo(3.2.1)octane-2-one as an oil and 7 g of 6(7)-hydroxy-2-methoxycarbonyl-8-azabicyclo-(3.2.1)octane-2-one as a crystalline solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; | A mixture of 2,5-dihydro-2,5-dimethoxy- furan (0.01 mol) and 4-amino-, (la,3a,4a,5i,7a)- tricyclo[3.3.1. 13,7]decan-l-ol (0.01 mol) in water (50 ml) was stirred at room temperature. Hydrochloric acid concentrated (2 ml) was added and the reaction mixture was stirred overnight. The acidic mixture was neutralized with an aqueous NaHC03 solution. This mixture was extracted with DCM (3 x). The combined organic layers were dried, filtered and the solvent evaporated, yielding 1.5 g of intermediate 13. |