114. Analgesics. Part II. The synthesis of amidone and some of its analogues

THE PHARMACOLOGY OF PHENADOXONE OR dl‐6‐MORPHOLINO‐4:4 — DIPHENYL — HEPTAN — 3 — ONE HYDROCHLORIDE

“…Holding that amidone in relation to its analgesic activity is unduly toxic, and that a substance with a higher margin of safety would be useful, we have examined a group of related compounds made in an attempt both to decrease the toxicity and to maintain or increase the analgesic activity. The chemistry of these compounds, together with their toxicities and analgesic activities, has already been reported by Dupre, Elks, Hems, Speyer, and Evans (1949) and Attenburrow, Elks, Hems, and Speyer (1949).…”

“…The chemistry of these compounds, together with their toxicities and analgesic activities, has already been reported by Dupre, Elks, Hems, Speyer, and Evans (1949) and Attenburrow, Elks, Hems, and Speyer (1949).…”

The First Asymmetric Halogen/Metal‐Exchange Reaction: Desymmetrization of Alcohols with Enantiotopic Bromoarene Substituents

“…Alcohols 11 and 12 as well as aminoalcohol 14 and (S)-2,2'-dihydroxy-1,1'-binaphthalene [(S)-BINOL (17 a)] were purchased. Aminoalcohols 13 a, [17] 13 b, [18] 13 c, [19] 13 d, [20] 15 a, [21] 15 b, [22] 16 a, [23] and 16 b [24] were prepared according to literature procedures, and (S)-BINOL-monoethers 17 b [25,26] and 17 c, d as well. [26] NHC precursor 21 is an elaborated 2-amino-2'-hydroxy-1,1'-binaphthalene (NOBIN) and was obtained by our recently developed synthesis [27] in 55 % overall yield, avoiding the lengthier previous synthesis.…”