Application of 87661-20-9,Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.
Step 1: A solution of n-butyl lithium in hexane (1.4M, 95.7 mL, 0.13 mol) was added drop wise to a solution of freshly distilled diisopropylamine (18.75 mL, 0.12 mol) in dry THF (400 mL) at -60 C. under nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (17.34 g, 0.12 mol) added drop wise over a period 30 min. Reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) reaction mixture was added drop wise 1,12-dibromododecane (40.0 g, 0.12 mol) in dry THF (40 mL) and DMPU (3.12 g, 0.02 mol). Then the temperature was allowed to reach room temperature and stirred at same temperature over a period of 16 h. The resulting reaction mixture was quenched with saturated NH4Cl (500 mL) at 0 C. and the reaction mixture was extracted with ethyl acetate (400 mL×3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (0.5% ethyl acetate in petroleum ether) to give product as pale yellow liquid 14.0 g (29%).1H NMR (300 MHz, DMSO-d6) delta (ppm): 1.55-1.61 (m, 2H), 1.08-1.12 (m, 2H), 1.35 (bs, 13H), 1.49 (bs, 16H), 1.64-1.89 (m, 2H), 3.42 (t, J=6.9 Hz, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl cyclopropanecarboxylate, its application will become more common.
Reference:
Patent; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
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