Synthesis of stable isotope labeled D9‐Mabuterol, D9‐Bambuterol, and D9‐Cimbuterol

Tu, Yahui; Zhong, Jiaqi; Wang, Haoran; Pan, Jie; Xu, Zhong; Yang, Weicheng; Luo, Yong

doi:10.1002/jlcr.3446

Cited by 12 publications

(23 citation statements)

References 10 publications

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“…1 H NMR (500 MHz, CDCl 3 ): δ (ppm) 7.94 (d, J = 7.7 Hz, 1H), 7.43 (t, J = 7.4 Hz, 1H), 7.38 (t, J = 7.2 Hz, 1H), 7.19 (d, J = 7.4 Hz, 1H) 2.36 (s, 3H). 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ (ppm) 144. 0, 134.1, 130.9, 130.8, 127.6, 123…”

Section: -Methyl-2-((methyl-d 3 )Sulfinyl)benzene (3b)mentioning

confidence: 99%

“…69−7.62 (m, 4H), 7.55−7.53 (m, 2H), 7.37−7.36 (m, 3H). 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ (ppm) 145.5, 132.5, 131.9, 128.9, 128.6, 126.5, 123.7, 122.7, 91.7, 88.3. IR (CH 2 Cl 2 , cm −1 ): 2970,2935,2885,1745,1467,1388,1094,1048,1008,842,762.…”

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ): δ (ppm) 7.67 (d, J = 8.4 Hz, 1H), 7.59 (d,J = 8.5 Hz,1H),2H). 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ (ppm) 137.4,132.7,129.8,125.3,125.1. IR (CH 2 Cl 2 , cm −1 ): 2974,2940,1479,1393,1092,1057,1013,829,765.…”

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ): δ (ppm) 7.90 (dd, J = 1.5, 7.8 Hz, 1H), 7.81 (d,J = 7.8 Hz,1H), 7.61 (t, J = 7.7 Hz, 1H), 7.22 (td, J = 1.5, 7.6 Hz, 1H). 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ (ppm) 148.3, 139.5, 132.6, 129.7, 125.9, 91.5, 41.9−41.4 (m, C−D 3 )sulfinyl)benzoatene (3n). The title compound 3n was prepared as described in the general procedure E using 2-((2-methoxy-2-oxoethyl)sulfinyl)benzoate (2n) (0.185 mmol, 1 equiv) as the starting material and purified by column chromatography on silica gel using 50% ethyl acetate/hexane (v/v) as the eluent.…”

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ) δ (ppm): 7.72 (d, J = 8.0 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 7.01 (s, 1H), 4.06− 3.98 (m, 2H), 3.19−3.13 (m, 1H), 2.90−2.82 (m, 2H), 2.62−2.56 (m, 1H), 2.34 (s, 6H), 1.59−1.54 (m, 2H), 1.38−1.30 (m, 2H), 0.91 (t, J = 7.3 Hz, 3H). 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ (ppm) 171. 6, 141.3, 137.9, 134.5, 131.7, 127.9, 124.1, 65.1, 49.2, 30.6, 26.3, 21.3, 19.2, 18.1, 13.8 2i).…”

mentioning

confidence: 99%

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Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

et al. 2023

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Deuterated organic molecules have immense value in the pharmaceutical industry. Here, we present a synthetic strategy for direct trideuteromethylation of sulfenate ions derived in situ from β-sulfinyl esters in the presence of a base utilizing inexpensive and abundant CD 3 OTs as the electrophilic trideuteromethylating agent. This protocol provides straightforward access to an array of trideuteromethyl sulfoxides in yields of 75−92% with a high degree of deuteration. The ensuing trideuteromethyl sulfoxide can be readily modified into trideuteromethyl sulfone and sulfoximine. Note pubs.acs.org/joc

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Section: -Methyl-2-((methyl-d 3 )Sulfinyl)benzene (3b)mentioning

confidence: 99%

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

Section: -((Methyl-d 3 )Sulfinyl)-4-(phenylethynyl)benzene (3i)mentioning

confidence: 99%

mentioning

confidence: 99%

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Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

et al. 2023

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The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD₃Reagents

Steverlynck

Sitdikov

Rueping

2021

Chemistry A European J

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In the field of medicinal chemistry, the precise installation of a trideuteromethyl group is gaining ever‐increasing attention. Site‐selective incorporation of the deuterated “magic methyl” group can provide profound pharmacological benefits and can be considered an important tool for drug optimization and development. This review provides a structured overview, according to trideuteromethylation reagent, of currently established methods for site‐selective trideuteromethylation of carbon atoms. In addition to CD3, the selective introduction of CD2H and CDH2 groups is also considered. For all methods, the corresponding mechanism and scope are discussed whenever reported. As such, this review can be a starting point for synthetic chemists to further advance trideuteromethylation methodologies. At the same time, this review aims to be a guide for medicinal chemists, offering them the available C−CD3 formation strategies for the preparation of new or modified drugs.

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Intramolecular Hiyama Coupling: Synthesis of 1,8,13‐Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer

Iwata

Hanada

Kumagai

et al. 2023

Chemistry A European J

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Herein, we describe Hiyama coupling via intramolecular substituent transfer from silicon on one blade of triptycenes to another to yield 1,8,13-trisubstituted chiral triptycenes. This reaction is attributed to the proximity effect of substituents on triptycene, which plays an important role in not only the formation of the oxy-palladacycle but also the activation of the silyl group to facilitate σ-bond metathesis. After bromination and nucleophilic ring opening, the second intramolecular Hiyama coupling provided various 1,8,13trisubstituted chiral triptycenes. The optical resolution of 1,8,13-triptycene afforded an optically active form for the first time.

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Synthesis of stable isotope labeled D₉‐Mabuterol, D₉‐Bambuterol, and D₉‐Cimbuterol

Cited by 12 publications

References 10 publications

Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD₃Reagents

Intramolecular Hiyama Coupling: Synthesis of 1,8,13‐Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer

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Synthesis of stable isotope labeled D9‐Mabuterol, D9‐Bambuterol, and D9‐Cimbuterol

Cited by 12 publications

References 10 publications

Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD3Reagents

Intramolecular Hiyama Coupling: Synthesis of 1,8,13‐Trisubstituted Chiral Triptycenes with Three Different Substituents by Intramolecular Substituent Transfer

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Product

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Synthesis of stable isotope labeled D₉‐Mabuterol, D₉‐Bambuterol, and D₉‐Cimbuterol

The Deuterated “Magic Methyl” Group: A Guide to Site‐Selective Trideuteromethyl Incorporation and Labeling by Using CD₃Reagents