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CAS No. : | 284492-22-4 | MDL No. : | MFCD02090669 |
Formula : | C14H18N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VSSDZTCJXHBUGF-UHFFFAOYSA-N |
M.W : | 310.30 | Pubchem ID : | 2756813 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
80% | With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; for 1.5h; | 20 g (95 mmol) of this intermediate and 31.2 g of di-tert-butyl dicarbonate were dissolved in 150 mL of a dioxane/water mixture (1 : 1) and 33 mL of DIEA were added. The mixture was stirred for about 90 min until full dissolution is observed. After solvent vaporation the remaining residue was dissolved in 1 L DCM and 3 times extracted with 500 mL of 5% citric acid. The organic phase was concentrated and the product precipitated with a mixture of DCM/diethylether/petrolether 1 : 1 : 1 and filtrated. After drying 23.5 g (80%) of the desired product were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | 5 g (16.1 mmol) of this intermediate and 3.095 g (23 mmol) (2R)-2-amino-2-phenylethanol were dissolved in acetonitrile and left at 0C for 3 days. The precipitate was filtered, dissolved in DCM and 2 times extracted with 5% citric acid. The organic phase was dried upon sodium sulfate and evaporated. This procedure was repeated twice. 1.52 g (30%) of the desired product were obtained with an ee of 95% and an [OC]D25 = +34.4 / methanol. 1500 mg (0.243 mmol) of this intermediate were dissolved in 100 mL methanol and hydrogenated on palladium/carbon for 30 min under normal pressure. The catalyst was separated off, the solution was concentrated, digested with diethyl ether, filtrated and the residue was dried in vacuo. 1334 mg (98%) of the title compound were obtained. [DC: (Dichlormethan/Methanol/Ammoniak (17%ig) (15:4:0.5); Rf= 0.18] |
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