Adding a certain compound to certain chemical reactions, such as: 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 143557-91-9, category: amides-buliding-blocks
To a stirred solution of Intermediate 63 (0.68 g, 2.98 mmol) in dry DMF (10 mL) wasadded NaH (60 % dispersion in mineral oil,120 mg, 3.00 mmol). After the mixturewas stirred for 15 mm Intermediate 26 (0.5 g, 2.29 mmol) was added as one portion. The resulting mixture was stirred at RT for 48 h. The reaction mixture was poured onto brine and extracted into EtOAc. The organic layer was washed with brine, separated, dried over MgSO4, filtered and concentrated under reducedpressure to give brown oil. The crude material was purified by Biotage Isolera chromatography (silica gel, eluting with heptane-EtOAc, 1:0 to 0:1) to afford 531 mg (54% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 7.71 (t, J = 1.4 Hz, 2H), 7.68 – 7.63 (m, 1H), 7.53 (d, J = 1.2 Hz, 1H), 7.13 (dd, J = 2.4, 1.3 Hz, 1H), 4.75 (tt, J = 10.6, 5.9Hz, 1H), 4.34 (5, 2H), 2.53 (d, J = 1.1 Hz, 3H), 2.20- 2.00 (m, 4H), 1.93 – 1.65 (m,4H), 1.49 (5, 9H).LCMS (Analytical Method A) Rt = 1 .46 mm, MS (ESIpos): m/z = 426.05 (M+H)+.
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Reference:
Patent; EVOTEC AG; DAVENPORT, Adam James; BRAEUER, Nico; FISCHER, Oliver Martin; ROTGERI, Andrea; ROTTMANN, Antje; NEAGOE, Ioana; NAGEL, Jens; GODINHO-COELHO, Anne-Marie; (703 pag.)WO2016/91776; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics