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The use of diborane and deuterodiborane in the synthesis of isotopically labeled amines
Author(s) -
Marshall Frederick J.,
McMahon Robert E.,
Lacefield William B.
Publication year - 1972
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590080312
Subject(s) - chemistry , diborane , pyridine , derivative (finance) , nitrile , amide , medicinal chemistry , amine gas treating , dimethyl sulfate , nitrogen , hydrogen halide , organic chemistry , boron , alkyl , halogen , financial economics , economics
The use of diborane has facilitated the preparation of several amines labeled with carbon‐14 or nitrogen‐15 by reduction of the corresponding labeled nitrile or amide. Its use was particularly advantageoue in the presence of aromatic halide substituents. Deuterodiborane, formed in situ from sodium borodeuteride and dimethyl sulfate, has been shown to be useful in the synthesis of 1, 1‐dideuteroamines. Amines prepared in this study include nortriptyline labeled with nitrogen‐15, deuterium or both,; 2‐(o‐chlorophenoxy) ethyl‐N‐cyclopropylamine as the 1‐ 14 C‐derivative and as the 1, 1‐dideutero derivative; 2‐(2, 4‐dichloro‐6‐phenylphenoxy) ethyl‐1‐ 14 C amine and its 2‐chloro‐6‐phenyl analog; and 3‐aminomethyl 14 C‐pyridine.