A two-step procedure to synthesize (3-fluoroadamantan-1-yl)methyl isocyanate from (3-hydroxyadamantane)acetic acid that involves fluorination with Ishikawa’s reagent on the first step of the synthesis was developed. The reaction of (3-fluoroadamantan-1-yl)methyl isocyanate with aliphatic diamines gave 1,3-disubstituted bis-diureas in 60–97% yields. A strong decrease in the melting points of the obtained ureas (up to ∼70–144 °C) was observed upon introduction of the fluorine atoms at the bridgehead positions of the adamantane unit.

中文翻译：

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1-[(3-fluoroadamantan-1-yl)methyl]-3-R-ureas和1,1'-(alkan-1,n-diyl)bis{3-[(3-fluoroadamantan-1)的合成及性质-yl)methyl]ureas}作为有前途的可溶性环氧化物水解酶抑制剂

开发了一种由 (3-羟基金刚烷) 乙酸合成 (3-氟金刚烷-1-基) 甲基异氰酸酯的两步程序，该程序涉及在合成的第一步中使用 Ishikawa 试剂进行氟化。(3-氟金刚烷-1-基)甲基异氰酸酯与脂肪族二胺的反应以 60-97% 的产率得到 1,3-二取代双脲。在金刚烷单元的桥头位置引入氟原子后，观察到所得尿素的熔点显着降低（高达~70-144°C）。