Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane

Kong, Han Il; Crichton, Jennifer E.; Manthorpe, Jeffrey M.

doi:10.1016/j.tetlet.2011.05.015

Cited by 19 publications

(11 citation statements)

References 17 publications

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“…Mass spectrum (EI, m/z): 8e: 163.0. Other resonances in PMR spectra of 7a-e and 8a-e agreed with those in the literature[17].Methyl-2-(9-demethoxyberberine bromide-9-yl)hydroxyacetate(4). A solution of 3·EtOH(3.10 g, 8.45 mmol) in CH 2 Cl 2 (50 mL) was treated with the methyl ester of bromoacetic acid (1.60 mL, 16.89 mmol), stirred on a magnetic stirrer, and refluxed for 7.5 h. The yellow precipitate was filtered off, refluxed with EtOH (100 mL), cooled, filtered off, and dried in vacuo to afford 4 (3.54 g, 89%), mp 254-256°C (dec.).…”

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confidence: 88%

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Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

et al. 2013

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547.978.1+547.833.8 V. G. Vasilcev, and N. F. Salakhutdinov 9-O-Acetamide analogs of berberine bromide were prepared in 20-87% yields via reaction of the isoquinoline alkaloid berberrubine with tertiary amides of bromoacetic acid. Aminolysis did not occur during reaction of methyl-2-(9-demethoxyberberine bromide-9-yl)hydroxyacetate with secondary amines. The corresponding acid or its ethyl ester was isolated.The leading cause of death (greater than 50% of all lethalities) in the majority of economically developed countries remains as before cardiovascular diseases (CVD) of atherosclerotic origin and their complications (acute myocardial infarct, sudden cardiac death). Hyperlipidemia and, in particular, hypercholesterolemia is the principal risk factor of atherosclerotic CVD. Drugs used in medical practice and developed to lower cholesterol can be divided into two classes that differ in principle according to their mechanism of action. The first class includes drugs that inhibit the synthesis of endogenous cholesterol. Such chemical compounds (e.g., statins) interrupt the synthetic pathway of cholesterol in vivo by blocking (mostly by a competing mechanism) the activity of the corresponding enzyme. The second class comprises compounds that regulate by one method or another the amounts of cholesterol already synthesized by the body or obtained in food and enable its amount to be maintained within acceptable limits.

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confidence: 88%

“…Amides of bromoacetic acid 7a-f were prepared by the literature method [16]. Spectral data agreed with those published [17].…”

Section: Methodssupporting

confidence: 72%

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

et al. 2013

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“…α-Trifluoromethylsulfonyl ketones, esters, and amides were prepared by displacement of the corresponding bromide ( Scheme 83 ) [ 112 , 118 ] or chloride ( Scheme 83 ,c) [ 118 – 119 ] under various conditions. Long reaction times and high temperatures were often required.…”

Section: Reviewmentioning

confidence: 99%

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

Guyon¹,

Cahard²

2017

Beilstein J. Org. Chem.

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Sodium trifluoromethanesulfinate, CF3SO2Na, and trifluoromethanesulfonyl chloride, CF3SO2Cl, are two popular reagents that are widely used for the direct trifluoromethylation of a large range of substrates. Further, these two reagents are employed for the direct trifluoromethylsulfenylation and trifluoromethylsulfinylation, the introduction of the SCF3 and the S(O)CF3 group, respectively. In addition to the aforementioned reactions, the versatility of these two reagents is presented in other reactions such as sulfonylation and chlorination. This first part is dedicated to sodium trifluoromethanesulfinate.

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“…This protocol was adapted from a literature procedure . The crude cyclohexyl diazoketone (0.1 g, 0.64 mmol) was dissolved in hexane (1.3 mL), and DCl (0.155 mL, 20% DCl in D 2 O, 0.98 mmol) was added slowly and vigorous gas evolution was observed.…”

Section: Methodsmentioning

confidence: 99%

Efficient, scalable and economical preparation of tris(deuterium)‐ and ¹³C‐labelled N‐methyl‐N‐nitroso‐p‐toluenesulfonamide (Diazald®) and their conversion to labelled diazomethane

Shields

Manthorpe

2014

Labelled Comp Radiopharmac

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A method for the preparation of multi-gramme quantities of N-methyl-d3-N-nitroso-p-toluenesulfonamide (Diazald-d3) and N-methyl-(13)C-N-nitroso-p-toluenesulfonamide (Diazald-(13)C) and their conversion to diazomethane-d2 and diazomethane-(13) C, respectively, is presented. This approach uses robust and reliable chemistry, and critically, employs readily commercially available and inexpensive methanol as the label source. Several reactions of labelled diazomethane are also reported, including alkene cyclopropanation, phenol methylation and α-diazoketone formation, as well as deuterium scrambling in the preparation of diazomethane-d2 and subsequent methyl esterification of benzoic acid.

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Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane

Cited by 19 publications

References 17 publications

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

Efficient, scalable and economical preparation of tris(deuterium)‐ and ¹³C‐labelled N‐methyl‐N‐nitroso‐p‐toluenesulfonamide (Diazald®) and their conversion to labelled diazomethane

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Stereoselective synthesis of ambiphilic alkenes via regioselective methylation of α-trifluoromethanesulfonyl carbonyl compounds with trimethylsilyldiazomethane

Cited by 19 publications

References 17 publications

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

Synthesis of berberine bromide analogs containing tertiary amides of acetic acid in the 9-O-position

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

Efficient, scalable and economical preparation of tris(deuterium)‐ and 13C‐labelled N‐methyl‐N‐nitroso‐p‐toluenesulfonamide (Diazald®) and their conversion to labelled diazomethane

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Product

Resources

About

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

Efficient, scalable and economical preparation of tris(deuterium)‐ and ¹³C‐labelled N‐methyl‐N‐nitroso‐p‐toluenesulfonamide (Diazald®) and their conversion to labelled diazomethane