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Synthese asymetrique de la D(+) amphetamine‐ 14 C‐7 par l'intermediaire du benzyl‐2 methyl‐2 dithianne‐l,3
Author(s) -
Pichat L.,
Beaucourt JP.
Publication year - 1976
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580120106
Subject(s) - chemistry , hydrogenolysis , medicinal chemistry , amine gas treating , yield (engineering) , chloride , benzyl alcohol , organic chemistry , catalysis , materials science , metallurgy
Benzyl chloride‐7‐ 14 C is condensed with 2‐lithio 2‐methyl 1,3‐dithianes. Deprotection with cupric chloride‐copper oxide of the resulting 2‐benzyl 2‐methyl 1,3‐dithianes leads to 1‐phenyl‐2‐propanone‐1‐ 14 C. The latter with L(‐)α‐methylbenzylamine in presence of molecuLar sieve gives rise to (‐)N‐(α‐phen‐ethyl)phenylisopropylimine which is catalytically reduced into the corresponding amine. Hydrogenolysis of this amine gives D(+) amphetamine‐7‐ 14 C isolated as the sulfate with an overall yield of 10 % based on benzoic acid‐7‐ 14 C specific activity: 27 mCi/mM.