Labelling of a new analgetic agent, 5α 9α‐dimethyl‐2‐[4‐(4‐fluorophenyl)‐4‐oxobutyl]‐2′‐hydroxy‐6,7‐benzo‐morphan (id‐1229), with tritium

Abstract

Abstract5α,9α‐Dimethyl‐2‐[4‐(4‐fluorophenyl)‐4‐oxobutyl]‐2′‐hydroxy‐6,7‐benzomorphan (X) (ID‐1229), a new analgetic agent, was labelled with tritium at C‐3, 4 or C‐3 position of the benzo‐morphan nucleus for the use of metabolic studies. The procedures used are illustrated in Fig. 2. Catalytic reduction of the enamine (VI) with tritium gas afforded the benzomorphan‐3,4‐3H (VIIa) in 24% radiochemical yield while reduction of VI with sodium borotritide gave the benzomorphan‐3‐3H (VIIb) in 40%. The tritiated benzomorphans (VIIa and VIIb) were easily converted to ID‐1229‐3,4‐3H (Xa) and ID‐1229‐3‐3H (Xb), respectively. The overall radiochemical yield of Xa was 7.5% based on tritium gas and that of Xb was 12.0% based on sodium borotritide.