Synthetic Route of 143557-91-9, These common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
[0178] A reaction flask was charged with crude compound 2 (5.5 g) in dry DMF (25 mL) under argon. NaH (60% in oil, 0.968 g, 24.2 mmol) was added in portions and the mixture was stirred at 50 C for 1 h. The mixture was cooled to rt and bromomethylcyclopropane (3.252 g, 24.2 mmol) was added followed by stirring at rt for 20 h under argon. The reaction mixture was quenched with water and the product extracted into ethyl acetate. The combined organic phases were dried over Na2S04, filtered, and concentrated. The product was purified by flash column chromatography (Si02; n-heptane/ethyl acetate 2: 1) to give the compound 3, 3a- cyclopropylmethoxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (3.354g). 1H NMR (CDCI3) delta 3.98 – 3.94 (m, 2H), 3.44 – 3.40 (m, 1H), 3.05 (d, 2H), 1.96 – 1.88 (m, 2H), 1.79 – 1.62 (m, 6H), 1.29 (s, 9H), 0.88 – 0.79 (m, 1H), 0.35 – 0.30 (m, 2H), 0.04 – 0.00 (m, 2H); 13C NMR (CDCI3) delta 153.4, 78.9, 73.0, 72.5, 52.7, 34.9, 28.5, 28.1, 10.9, 2.8.
Statistics shows that tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate is playing an increasingly important role. we look forward to future research findings about 143557-91-9.
Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; ESKILDSEN, Jorgen; OLSSON, Roger; LUHRS, Lauren, M.; WHEELER, Larry, A.; GIL, Daniel, W.; WO2014/152144; (2014); A1;,
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