Iodomethane (purum), potassium carbonate (p.a.), IPNS (Deterenol acetate), 3‐chloroperbenzoic acid (<77%), acetone, lithium aluminium hydride (powder, 95%), potassium carbonate (>99%), sulfur trioxide pyridine complex (97%), and octopamine hydrochloride (analytical standard) were obtained from Sigma‐Aldrich (Deisendorf, Germany), acetonitrile, formic acid, and ammonium acetate (all analytical grade) were purchased from Merck (Darmstadt, Germany), and solid‐phase extraction cartridges (OASIS HLB, 3 mL, 60 mg sorbent) were obtained from Waters (Eschborn, Germany). The internal standard IPNS‐d7 (deterenol‐d7) was provided by LGC Standards GmbH (Wesel, Germany).
Lithium aluminium hydride
Manufactured by Merck Group
Sourced in Germany, United States
Lithium aluminium hydride is a reducing agent used in organic synthesis. It is a white, crystalline solid that reacts with water to produce hydrogen gas. The compound is commonly used in the reduction of carbonyl compounds, such as aldehydes and ketones, to alcohols.
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Lab products found in correlation
Acetonitrile, by Merck Group (1 mentions)
Acetone, by Merck Group (1 mentions)
Ammonium acetate, by Merck Group (1 mentions)
Potassium carbonate, by Merck Group (1 mentions)
Sulfur trioxide pyridine complex, by Merck Group (1 mentions)
Octopamine hydrochloride, by Merck Group (1 mentions)
Formic acid, by Merck Group (1 mentions)
3 chloroperbenzoic acid, by Merck Group (1 mentions)
N butyllithium, by Merck Group (1 mentions)
Nicolet is50 ft ir, by Thermo Fisher Scientific (1 mentions)
Avance 3 600 mhz spectrometer, by Bruker (1 mentions)
Silica gel, by Merck Group (1 mentions)
Cdcl3, by Merck Group (1 mentions)
Amines, by Merck Group (1 mentions)
Arx 300 mhz nmr spectrometer, by Bruker (1 mentions)
Hydrogen peroxide 30 aqueous solution, by Sinopharm (1 mentions)
N n dimethylformamide (dmf), by Sinopharm (1 mentions)
Dimethyl sulfoxide (dmso), by Sinopharm (1 mentions)
Thioglycolic acid, by Merck Group (1 mentions)
Triphosgene, by Merck Group (1 mentions)
6 protocols using lithium aluminium hydride
1
Quantitative Analysis of Deterenol Acetate
2
Synthesis of Rare-Earth Organometallic Complexes
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All manipulations were performed under an atmosphere of dry, oxygen-free argon, using either standard Schlenk techniques or an argon-filled glove box. Toluene and thf, and their deuterated analogues for NMR spectroscopy, were dried by refluxing over potassium and collected by distillation. All solvents were stored over activated 4 Å molecular sieves and freeze-thaw degassed before use. Anhydrous rare-earth chlorides (99.99% purity) were purchased from Strem Chemicals. n-Butyllithium (1.6 M in hexanes), phosphorus(III) chloride, lithium aluminium hydride, mesitylmagnesium bromide (1.0 M in thf) and di-methylcyclopentadiene (90%) were purchased from Sigma-Aldrich. Mesitylphosphine44 , the sodium salt of methylcyclopentadienide45 , and rare-earth tris(methylcyclopentadienide) complexes were synthesised according to the literature procedures46 . Elemental analyses were carried out by Mr Stephen Boyer at London Metropolitan University, UK
3
Synthesis of Cage Dimer Compounds
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Seventy micromole of the respective cage dimer 2 were dissolved in dried THF. After fumigating of the solution with argon it was stirred and cooled down to −8 °C. Then 1.12 mmol of lithium aluminium hydride (Sigma Aldrich, St. Louis, MO, USA) were added dropwise as a one molare solution in THF under stirring for additional three hours at the low temperature. The reaction was followed by the use TLC. After a complete disappearance of the starting compound on the TLC sheet portions of a 20% solution of potassium hydroxide and of ice water were added at a temperature of 0 °C. Then the organic layer was extracted with chloroform for several times. The organic layer was unified, dried over sodium sulfate and filtered. Then the solution volume was reduced under low pressure and a mixture of chloroform, diethyl ether and petrol ether was added dropwise. The precipitated target compounds 3a –k were recrystallized from methanol.
4
Synthesis of Substituted Amines via Reduction
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The reagents were purchased and used without purification. Lithium aluminium hydride, reagent grade 95%; pyridinium chlorochromate, 98%; thionyl chloride; silica gel, 200–400 mesh, 60 Å for column chromatography; CDCl3 for NMR spectroscopy; and amines were supplied by Sigma Aldrich, Darmstadt, Germany. Other reagents were provided by Chempur, Piekary Śląskie, Poland. TLC sheets Alugram SIL G/UV254 were obtained from Mecherey-Nagel, Germany.
NMR spectra were recorded on a Bruker ARX 300 MHz NMR Spectrometer. Chemical shifts (δ in ppm) were obtained from internal solvent-CDCl3 7.26 ppm for 1H. 13 C and 19F NMR spectra were acquired on a Bruker Avance III 600 MHz spectrometer (Bruker Biospin GmbH, Ettlingen, Germany). Abbreviations used in NMR spectra: s—singlet, d—doublet, t—triplet, q—quartet, sx—sextet, m—multiplet. HR-MS spectra were recorded on a Bruker Daltonic model Compact, using the ESI technique. IR spectra were recorded on a Thermo Scientific Inc. (Waltham, MA, USA) model Nicolet iS50 FT-IR using the ATR technique.
NMR spectra were recorded on a Bruker ARX 300 MHz NMR Spectrometer. Chemical shifts (δ in ppm) were obtained from internal solvent-CDCl3 7.26 ppm for 1H. 13 C and 19F NMR spectra were acquired on a Bruker Avance III 600 MHz spectrometer (Bruker Biospin GmbH, Ettlingen, Germany). Abbreviations used in NMR spectra: s—singlet, d—doublet, t—triplet, q—quartet, sx—sextet, m—multiplet. HR-MS spectra were recorded on a Bruker Daltonic model Compact, using the ESI technique. IR spectra were recorded on a Thermo Scientific Inc. (Waltham, MA, USA) model Nicolet iS50 FT-IR using the ATR technique.
5
Synthesis of HCPT-Loaded PEI Nanoparticles
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1,1′-Carbonyldiimidazole, (CDI, 97%), hydroxycamptothecin (HCPT), branched polyethylenimine (PEI, Mw = 1800 Da), thioglycolic acid, 1,7-heptanediol, triphosgene, bismuth chloride, 2,2-dimethoxypropane, and lithium aluminium hydride, were purchased from Sigma-Aldrich Chemical (St. Louis, MO, USA). Hydrogen peroxide 30% aqueous solution, dimethyl sulfoxide (DMSO), acetonitrile, tetrahydrofuran (THF), dichloromethane (DCM), diethyl ether, and N,N-dimethylformamide (DMF), were purchased from Sinopharm Chemical Reagent Co., Ltd (China). 3-(4,5-Dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide (MTT), and 5-fluorocytosine were obtained from Aladdin Chemical Reagent Co., Ltd (China). Dulbecco's Modified Eagle's Medium (DMEM), Roswell Park Memorial Institute 1640 (RPMI-1640), fetal bovine serum (FBS), penicillinestreptomycin and trypsin were purchased from Genom Technology Co., Ltd (China).
6
Synthesis of 1,18-Octadecanedioic Acid
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All chemicals were used as received without further purification. 1,18-octadecanedioic acid was purchased from Elevance Renewable Sciences Inc. Titanium(IV) n-butoxide (97 %), lithium aluminium hydride (95 %), lithium hydride (95 %), diethyl carbonate (≥ 99 %), potassium hydroxide (≥ 99 %) and mEthanol (≥ 99.8 %) were purchased from Sigma Aldrich. Ethanol (≥ 99.8 %), xylene (isomeric mixture, ≥ 99 %) and tetrahydrofuran (≥ 99.5 %) were purchased from Carl Roth. 2-Propanol (≥ 99.7 %) was purchased from VWR and toluene (≥ 99.9 %) was purchased from Merck. N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) (98%) was purchased from abcr.
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