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CAS No. : | 39961-95-0 | MDL No. : | MFCD00191979 |
Formula : | C10H20N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GDOTUTAQOJUZOF-ZXZVGZDWSA-N |
M.W : | 264.28 | Pubchem ID : | 11448443 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
70% | (R,R)-N,N'-Bis(5-3-tert-butyl-salicylidene)-l,2-cyclohexanediamine was synthesized following a similar procedure described by Jacobsen E. N., Zhang W., Muci A. R., Ecker J. R., and Deng L. Highly Enantioselective Epoxidation Catalysts Derived from 1,2- Diaminocyclohexane, J. Am. Chem. Soc, 113, 7063-7064 (1991). To a 250 mL round bottom flask was added 2.0053 g (8.5573 mmol) of 3,5 -tert butyl-2-hydroxybenzaldehyde that was dissolved in 20 mL absolute ethanol. Concurrently, (R5R)- 1,2-diammoniumcyclohexane mono-(+)-tartrate salt {see Larrow J. F., Jacobsen E. N., Gao Y., Hong Y., Nie X., and Zepp C. M., A Practical Process for the Large-Scale Preparation of (R,R)-N,N'-Bis(3,5-Di-tert- butylsalicylidene)-l,2-Cyclohexanediaminomanganese (III) Chloride, a Highly Enantioselective Epoxidation Catalyst, J. Org. Chem., 59, 1939-1940 (1994); (1.1219 g, 4.2451 mmol) was dissolved in a basic (NaOH) 0.2 M aqueous/absolute ethanol solution (1 :2). This salt solution was added dropwise to the benzaldehyde solution and the mixture was refluxed under nitrogen for 1 hour. The reaction mixture was filtered using a 60 mL medium frit and washed with 95% ethanol. The product was then extracted into methylene chloride. The frit was washed with additional methylene chloride until the solid was colorless. The solvent was removed under reduced pressure to yield 1.6843 gm (70%) of a yellow solid. 1H NMR: (CDCl3, ppm) delta = 1.24 (s, 9H); 1.41 (s, 9H); 1.45 (m, IH); 1.65 - 1.8 (m, IH); 1.8 - 2.0 (m, 2H); 3.32 (m, IH); 6.98 (d, IH); 7.30 (d, IH); 8.30 (s, IH); 13.72 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 90 percent / K2CO3 / H2O; ethanol / 5 h / Heating 2.1: KHCO3; Oxone / acetonitrile; tetrahydrofuran; H2O / 3 h / 20 °C 3.1: benzyloxyhydroxylamine hydrochloride; aq. HCl / methanol / 0.33 h 4.1: 3.85 g / Et3N; DMAP; imidazole / CH2Cl2 / 2 h / 20 °C 5.1: DIEA / CH2Cl2 / 72 h 5.2: 55 percent / aq. HCl / CH2Cl2 / 0.5 h | ||
Multi-step reaction with 6 steps 1: K2CO3 / H2O; ethanol / 5 h / Heating 2: oxone; aq. KHCO3 / acetonitrile; tetrahydrofuran / 2.25 h / 20 °C 3: benzyloxyhydroxylamine hydrochloride; HCl / methanol / 0.33 h 4: Et3N; DMAP; imidazole / CH2Cl2 / 16 h / 20 °C 5: DIEA / CH2Cl2 6: aq. HCl / CH2Cl2 / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 90 percent / K2CO3 / H2O; ethanol / 5 h / Heating 2.1: KHCO3; Oxone / acetonitrile; tetrahydrofuran; H2O / 3 h / 20 °C 3.1: benzyloxyhydroxylamine hydrochloride; aq. HCl / methanol / 0.33 h 4.1: 3.85 g / Et3N; DMAP; imidazole / CH2Cl2 / 2 h / 20 °C 5.1: DIEA / CH2Cl2 / 72 h 5.2: 72 percent / aq. HCl / CH2Cl2 / 0.5 h | ||
Multi-step reaction with 6 steps 1: K2CO3 / H2O; ethanol / 5 h / Heating 2: oxone; aq. KHCO3 / acetonitrile; tetrahydrofuran / 2.25 h / 20 °C 3: benzyloxyhydroxylamine hydrochloride; HCl / methanol / 0.33 h 4: Et3N; DMAP; imidazole / CH2Cl2 / 16 h / 20 °C 5: DIEA / CH2Cl2 6: aq. HCl / CH2Cl2 / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water / Inert atmosphere 2: dichloromethane / 0.5 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium carbonate In ethanol; water at 20℃; for 24h; | Synthesis of ligand 1 A mixture of 0.26 g (0.979 mmol) of (1R,2R)-cyclohexane diamine mono-l-tartrate and 0.27 g (1.958 mmol) of potassium carbonate was dissolved in 3 ml of 50% aqueous ethanol solution. The resulting mixture was added to a suspension of 0.335 g (0.979 mmol) of (R)-3,3′-diformyl-BINOL in 7 ml of ethanol. The reaction mixture was stirred at room temperature for 24 h. The resulting precipitate was filtered of and washed with ethanol and dried under vacuum. Yield of light-yellow solid was 0.5g (61%). 1H NMR (400MHz, CDCl3) δ 13.21 (br s, 4H), 8.47 (s, 4H), 7.75 (m, 8H), 7.28 (m, 4H), 6.96 (m, 8H), 3.31 (m, 4H), 1.82-1.92 (m, 8H), 1.40-1.61 (m, 8H). [α]D25=-214 (c 0.25, CH2Cl2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In water at 20℃; for 24h; | Synthesis of aquated active componentof oxaliplatin The active component of oxaliplatin, [Pt(H2O)2(R,R-dach)](NO3)2, was synthesised using an adaptation of a previouslyreported method [32]. K2[PtCl4] (500 mg, 1.2 mmol) wasdissolved in ~ 50 mL water, with an equimolar quantity of theL-tartrate salt of 1R,2R-dach (317 mg, 1.2 mmol) and 4 mol.equiv. of TEA (670 μL, 4.8 mmol), at room temperature. Thesolution was stirred for 24 h, until a yellow coloured precipitate[PtCl2(R,R-dach)] was produced. [PtCl2(R,R-dach)]was collected by vacuum filtration, and washed with waterand methanol, before air drying. The precipitate (~ 248 mg,0.65 mmol) was added to water (~ 100 mL) with 1.9 mol.equiv. of AgNO3(210 mg, 1.24 mmol). The solution was then stirred at a temperature of approximately 85 °C for24 h, in the absence of light. The resultant white-colouredprecipitate (AgCl) was then removed by vacuum filtration.Finally, the filtrate was rotary evaporated to dryness toyield faintly yellow-coloured [Pt(H2O)2(R,R-dach)](NO3)2(244 mg, 0.52 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: sodium hydroxide / dichloromethane / 18 h / 25 °C 2: hydrogenchloride / methanol / 2 h / 25 °C 3: potassium carbonate / acetonitrile / 24 h / Reflux 4: trifluoroacetic acid / dichloromethane / 4 h / 25 °C 5: dichloromethane / 26 h / 25 °C |
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