Synthesis of a stable iminium salt and propellane derivatives.
The treatment of morphinan 1 with NaH and MsCl provided very stable iminium salt 7 possessing propellane skeleton. One of the synthesized iminium salts 7, isobutyl derivative 7b, was crystallized and its structure was determined by X-ray crystallography. The natural bond orbital analysis suggested that the stability of the iminium should result from the stereoelectronic effect (hyperconjugation) attributed to their own structures.
Nagase
Hiroshi
H
School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan. nagaseh@pharm.kitasato-u.ac.jp
Yamamoto
Naoshi
N
Nemoto
Toru
T
Yoza
Kenji
K
Kamiya
Kenshu
K
Hirono
Shuichi
S
Momen
Shinobu
S
Izumimoto
Naoki
N
Hasebe
Ko
K
Mochizuki
Hidenori
H
Fujii
Hideaki
H
D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008698:Mesylates / Q000737:chemistry; D009019:Morphinans / Q000138:chemical synthesis* / Q000737:chemistry; D017670:Sodium Compounds / Q000737:chemistry
D000701:Analgesics, Opioid; D008698:Mesylates; D009019:Morphinans; D017670:Sodium Compounds; C524957:sodium hydride; C030209:methanesulfonyl chloride