Excess methyllithium is then added to create methyl ketones which when reduced with lithium aluminum hydride gives the amine group.The synthesis pictured to the left is a synthesis of rimantadine as synthesized in Europe

History
Rimantadine was discovered in 1963 and patented in 1965 in the US by William W. Prichard in Du Pont & Co., Wilmington, Delaware (patent on new chemical compound U.S. Patent 3,352,912, 1965 and on the first method of synthesis U.S. Patent 3,592,934, 1967). Prichards methods of synthesis of rimantadine from the corresponding ketone oxime were based on its reduction with lithium aluminum hydride. See also
Adapromine
Bromantane
Memantine
Tromantadine

Synonyms
1-(1-Adamantyl)ethanamine, 1-(Adamantan-1-yl)ethanamine, 1-(adamantan-1-yl)ethan-1-aminem, alpha-Methyl-1-adamantanemethylamine, alpha-Methyladamantanemethylamine, Rimantadine [INN:BAN], Rimantadinum [INN-Latin], 1-(1-Adamantyl)ethylamin, Remantadine, Rimantadina [INN-Spanish], 1-Adamantan-1-yl-ethylamine, RIMANTADIN, HSDB 7438, CHEMBL959, BRN 2715740, 1-Adamantanemethylamine, .alpha.-methyl-, .alpha.-Methyladamantanemethylamine, 1-(1-adamantyl)-ethylamine, 1-(tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanamine, Riamantadine, Rimantadina, Rimantadinum, Tricyclo(3.3.1.13,7)decane-1-methanamine, alpha-methyl-, [1-(1-adamantyl)ethyl]amine hydrochloride, Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, alpha-methyl-, 1-ADAMANTANEMETHYLAMINE, alpha-METHYL-, 1-Rimantadine, 887336-05-2, Tricyclo[3.3.1.13,7]decane-1-methanamine, a-methyl-, Rimant, 1-(1-adamantyl)ethylamine, Rimantadine (INN), Enamine_005755, NCGC00159491-02, Rimant & .alpha.
IFN, Rimantadine (Flumadine), Rimantidine & .alpha.IFN, 1-Adamantan-1-ylethylamine, rimantidin, Rimantadin A, (R)-1-(Adamantan-1-yl)ethan-1-amine, 1-adamantanylethylamine, Maybridge1_002066, SCHEMBL2981, 1-tricyclo[3.3.1.1~3,7~]dec-1-ylethanamine, Oprea1_602732, SCHEMBL2619249, CHEMBL1201272, DTXSID2023561, SCHEMBL20409367, CHEBI:94440, CTK6A4437, HMS1410F13, HMS2090L19, HMS3604N13, HMS3655J05, 1-Adamantanemethylamine, ?-methyl-, ALBB-013870, BCP12269, HY-B0338, ZX-AN012619, ANW-72018, BBL013215, BDBM50216627, MFCD00869344, s1964, STK177253, (alpha-methyl-1-adamantyl)methylamine, AKOS000264537, AKOS006238592, AKOS016038537, .alpha.-Methyl-1-adamantanemethylamine, AM84461, API0024288, BBV-156986, CCG-236078, CS-2380, DB00478, FCH3207896, MCULE-9027470290, IDI1_007990, NCGC00159491-03, NCGC00159491-05, AK-58175, AS-68744, CC-34261, LS-15019, OR315791, SBI-0206810.P001, AB0012750, AX8049536, DB-042207, FT-0630403, H6325, ST45025920, SW220023-1, EN300-33990, C07236, D08483, Q421711-[(3R,5S,7s)-adamantan-1-yl]ethan-1-amine, AB00638368-09, AB00959689-03, AB01506092_02, AB01506092_03, 392R284, C-06592, BRD-A84282119-003-01-2, Z56757137, 1-(Tricyclo[3.3.1.1>3,7>]dec-1-yl)ethanamine (HCl), Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl-, 1-(1-Adamantyl)ethylamine Hydrochloride;Rimantadine hydrochloride, Tricyclo(3.3.1.1(sup 3,7))decane-1-methanamine, .alpha.-methyl-, Tricyclo[3,3,1,1(3,7)]decane-1-methanamine, .alpha.-methyl-, Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl- & IFN.alpha

References
External links
U.S. FDA press release announcing rimantadines approval
U.S. Center for Drug Evaluation and Research rimantadine description
U.S. NIH rimantadine description
U.S. CDC flu anti-viral treatment information