Preparation of ring labelled adamantane derivatives II. 2‐adamantanone‐2− 14 C, adamantane‐2− 14 C and 1‐methyladamantane‐2 or 4− 14 C
1971; Wiley; Volume: 7; Issue: 1 Linguagem: Inglês
10.1002/jlcr.2590070102
ISSN1559-0860
AutoresSamuel H. Liggero, Zdenko Majerski, Paul von Ragué Schleyer, Alfred P. Wolf, Carol S. Redvanly, Hans Wynberg, J. A. Boerma, J. Strating,
Tópico(s)Hormonal Regulation and Hypertension
ResumoAbstract A high‐yield, relatively simple synthetic route leading to incorporation of 14 C into the secondary position of the adamantane nucleus is described. The synthesis was achieved by the sequence shown in Figure 2. The key steps involved the introduction of a 14 C label by diazomethane‐ 14 C ring expansion of adamantanone to give 4‐homoadamantanone‐4− 14 C (I). Benzylic acid rearrangement of the corresponding homoadamantane diketone (II) gave hydroxy acid (III) which was converted by a novel reaction (SOCl 2 /benzene) to 2‐adamantanone‐2− 14 C (IV). The overall yield of labelled 2‐adamantanone was 66%. Wolff‐Kishner reduction of (IV) gave adamantane‐2− 14 C (V). This was converted to the l‐methyl derivative (VII) by treatment of the corresponding bromide (VI) with methylmagnesium bromide.
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