The Synthesis of (±), (+) and (-) α-(3- Thiamorpholinyl)-benzhydrol, a New Selective Stimulant of the Central Nervous System

Abstract

The Synthesis of (±), (+) and (-) a-(3-

Discovery and Synthesis of HIV Integrase Inhibitors: Development of Potent and Orally Bioavailable N-Methyl Pyrimidones

“…Nitrile 62b was prepared from the ethyl thiomorpholine carboxylate 72 obtained according literature procedure. 44 Nitrile 62c was synthesized from the oxygenated pipecolic acid derivative 75 that was obtained according to a literature procedure 45…”

“…To a solution of ethyl thiomorpholine-3-carboxylate 72 44 (15.5 g, 0.11 mol) in CHCl 3 , NaHCO 3 (9.2 g, 0.11 mol), and NaCl (22 g) in H 2 O (168 mL), followed by (Boc) 2 O (26.4 g, 0.12 mol), were added. The reaction mixture was stirred at reflux for 4 h. The aqueous phase was washed with CHCl 3 , and the organic phase was washed with brine, dried (Na 2 SO 4 ), and evaporated under reduced pressure.…”

Absolute configurations of the enantiomeric pheniramines, methylphenidates, and pipradrols

“…Accordingly, the absolute configuration of the the more active (2,5) levorotatory pipradrol hydrochlorides and their dextrorotatory free bases is (R). The absolute configuration of V, VI, and VII is (2s: 2'R) while the base-catalyzed epimerization (6) of VT to the (+)-threo-amide and conversion of the latter to the corresponding (+)-threo-acid (cf.…”

Phenylalkylamines

“…Because of the pronounced biological effects exhibited by di-(phenylalky1)amines (111) and because of the desirable properties elicited by the incorporation of the alkylamine portion in a cyclic structure (8), it was of interest to prepare both monoand di-(phenylalky1)amines containing the pyridine and piperidine ring (Tables I and 111). The compounds listed in Table 111 also bear some structural similarity to the alkaloid lobeline (IV) (9).…”