4-Homoadamantyl cation. II. Mechanistic studies on Lewis acid catalyzed conversion of homoadamantene to 2-methyladamantane by carbon-13 labeling techniques. Convenient synthesis of 4-homoadamantanone-5-13C and homoadamantene-4-13C

Mlinaric-Majerski, K.; Majerski, Zdenko; Pretsch, E.

doi:10.1021/jo00913a033

Cited by 9 publications

(1 citation statement)

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“…The generation and use of TMS‐protected cyanohydrins has been reported several times with labeled compounds. This includes steroids, substituted acetophenones, ethyl 2‐ethylacetoacetate, and adamantanone; however, only in the adamantane example was a labeled version of TMS‐CN used. The authors report the synthesis of TMS‐ 13 CN from K 13 CN via Ag 13 CN.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Lindelöf

Ericsson

Simonsson

et al. 2016

Labelled Comp Radiopharmac

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An AstraZeneca effort to identify a 5-lipoxygenase activating protein inhibitor with good drug-like properties resulted in the identification of AZD6642. To further understand its drug metabolism and pharmacokinetic properties, it was required labeled with tritium. The tritiation of AZD6642 was effected by Ir-catalyzed exchange chemistry to give an average of one tritium per molecule. Additionally, a stable isotope labeled version of AZD6642 was required to support bioanalytical studies. The synthesis originated from [(2) H6 ]acetone which was converted to the trimethylsilyl cyanide adduct and subsequently reduced to give 2-(aminomethyl)-[1,1,1,3,3,3-(2) H6 ]propan-2-ol in good yield. Carbonylation to give an amide adduct resulted in an intermediate that was converted to the final compound in four steps.

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Section: Resultsmentioning

confidence: 99%

Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Lindelöf

Ericsson

Simonsson

et al. 2016

Labelled Comp Radiopharmac

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Synthesis of adamantane derivatives—38

1978

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Synthetic approaches to large diamondoid hydrocarbons

McKervey

1980

Tetrahedron

103

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4-Homoadamantyl cation. II. Mechanistic studies on Lewis acid catalyzed conversion of homoadamantene to 2-methyladamantane by carbon-13 labeling techniques. Convenient synthesis of 4-homoadamantanone-5-13C and homoadamantene-4-13C

Cited by 9 publications

References 2 publications

Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Synthesis of adamantane derivatives—38

Synthetic approaches to large diamondoid hydrocarbons

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4-Homoadamantyl cation. II. Mechanistic studies on Lewis acid catalyzed conversion of homoadamantene to 2-methyladamantane by carbon-13 labeling techniques. Convenient synthesis of 4-homoadamantanone-5-13C and homoadamantene-4-13C

Cited by 9 publications

References 2 publications

Synthesis of [3H] and [2H6]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Synthesis of [3H] and [2H6]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Synthesis of adamantane derivatives—38

Synthetic approaches to large diamondoid hydrocarbons

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Product

Resources

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Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)

Synthesis of [³H] and [²H₆]AZD6642, an inhibitor of 5‐lipoxygenase activating protein (FLAP)