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The synthesis of 14 C and 3 H‐labeled N‐(2‐ p ‐azidophenylethyl)‐norlevorphanol
Author(s) -
Degraw J. I.,
Engstrom J. S.
Publication year - 1975
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.2590110208
Subject(s) - chemistry , nitrobenzene , moiety , alcohol , ethanol , chloride , medicinal chemistry , nitro , sodium , sodium acetate , nuclear chemistry , stereochemistry , organic chemistry , catalysis , alkyl
Synthetic procedures for N‐(2‐ p –azidophenylethyl)‐norlevorphanol ( 9 ) labeled with 14 C and 3 H at the 1‐position of the 2‐phenylethyl moiety are presented. A process for synthesis of p ‐nitrophenylacetic‐1‐ 14 C acid from p ‐chloro‐nitrobenzene and methyl cyano‐ 14 C‐acetate is described. The nitro acid was converted to 9 in a six step procedure, proceeding through 2‐( p ‐aminophenyl)ethanol ( 6 ) as a key intermediate. The alcohol ( 6 ) was also prepared with 3 H label via reduction of methyl p ‐aminophenylacetate with sodium borotritide‐aluminium chloride.