MOSE

4,4'-(Selenodi-2,1-ethanediyl)bismorpholine dihydrochloride; Bis(beta-morpholinoethyl)selenide dihydrochloride

83616-20-0, 73511-88-3 ([75Se]-labeled)

C12-H24-N2-O2-Se.2-Cl-H

380.2154

State University of New York, Buffalo (Originator)

DIAGNOSTIC AGENTS, Radiopharmaceuticals, Radiopharmaceuticals for Brain Imaging

Biological Testing

　

Drugs Fut

Mose

Selenious acid (H2SeO3) is successfully reduced by sodium borohydride (in excess) to form NaHSe (II). After reacting with beta-morpholinoethyl chloride (III) the bis(beta-morpholinoethyl)selenide is the only product and no diselenide is isolated. The unreacted NaHSe is reoxidized during the workup to insoluble Sex, which is easily separated by filtration. The product is separated from unreduced H2SeO3 by chloroform extraction. This procedure is also useful for the preparation radioactive MOSE using Se-75 (t1/2 = 120 days). The purity of the extracted material is 95%.

Kung, H.F.; Kostyniak, P.J.

Kung, H.F.; Kostyniak, P.J.; Mose. Drugs Fut 1985, 10, 9, 748

Drugs Fut1985,10,(9):748

Synthesis of 090973: Selenious acid (H2SeO3) (1) is successfully reduced by sodium borohydride (in excess) to form NaHSe (II). After reacting with beta-morpholinoethyl chloride (III) the bis(beta-morpholinoethyl)selenide is the only product and no diselenide is isolated. The unreacted NaHSe is reoxidized during the workup to insoluble Sex, which is easily separated by filtration. The product is separated from unreduced H2SeO3 by chloroform extraction. This procedure is also useful for the preparation radioactive MOSE using Se-75 (t1/2 = 120 days). The purity of the extracted material is 95%. (Scheme 09097301a) Manufacturer Farmitalia Carlo Erba (Italy) Reference 1. Gandolfi, C., Pellegatta, R., Faustini, F. and Fumagalli, A.; US 4.293.705.

US 4293705

13,14-Dehydro-11-deoxy-prostaglandins and process for their preparation

Selenious acid (H2SeO3) is successfully reduced by sodium borohydride (in excess) to form NaHSe (II). After reacting with beta-morpholinoethyl chloride (III) the bis(beta-morpholinoethyl)selenide is the only product and no diselenide is isolated. The unreacted NaHSe is reoxidized during the workup to insoluble Sex, which is easily separated by filtration. The product is separated from unreduced H2SeO3 by chloroform extraction. This procedure is also useful for the preparation radioactive MOSE using Se-75 (t1/2 = 120 days). The purity of the extracted material is 95%.

Gandolfi, C.; Pellegata, R. Fumagalli, A. (Pharmacia & Upjohn SpA)

Gandolfi, C.; Pellegata, R. Fumagalli, A. (Pharmacia & Upjohn SpA); 13,14-Dehydro-11-deoxy-prostaglandins and process for their preparation. US 4293705

US 4293705,,():

Synthesis of 107351: The synthetic route from (-)-(5-alfa-hydroxy-2-beta-formylcyclopentan-1-a-yl]acetic acid gamma-Iactone (IV) to title compound is depicted in Scheme 10735101a: The condensation of (+)-2S-2-methylhexanoate (I) with dimethyl methylphosphonate (II) by means of butyllythium in THF gives dimethyl-2-oxo-3S-methylheptylphosphonate (III). A Wittig reaction of (III) with the gamma-Iactone (IV) by means of sodium hydride in dry toluene yields the keto lactone (V) which is brominated with pyridinium hydrobromide perbromide in pyridine to give the alfa-bromoketo Iactone (VI). Compound (VI) is reduced with sodium borohydride in methanol to yield the bromohydroxy lactone (VII). The hydroxy group of compound (VII) is protected with dihydropyrane giving (VIII), which is reduced with diisobutylaluminum hydride in toluene to yield the hemiacetal (IX). The alfa-chain is introduced by a Wittig condensation of (IX), with the ylide obtained by reacting the 4-carboxybutyltriphenylphosphinium bromide with potassium tert-butoxide in DMSO, and at the same time dehydrohalogenation occurs and the acetylenic bond is formed to yield (5Z,9S,15S,16S)-9,15-dihydroxy-16-methyl prost-5-en-13-ynoic acid-15-tetrahydropyranyloxy (X). Sequential esterification of (XI) with methyliodide and potassium carbonate in DMF and oxidation with Jones' reagent in acetone gives the 9-oxoprostaglandin (XII), which is deprotected with acetic acid to afford the final compound. Description Colorless oil.