Electric Literature of 80466-51-9 ,Some common heterocyclic compound, 80466-51-9, molecular formula is C11H17NO, 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.
General procedure: The solution of boronic acid 4 (9.4 mg, 0.025 mmol, 5 mol%) and aminoalcohol (5.2 mg, 0.025 mmol, 5 mol%) was refluxed in toluene for12 h to remove water azeotropically. The mixture was allowed to coolto r.t. and toluene was removed in vacuo. Next, 1 M SnCl4 in CH2Cl2(25 muL, 0.025 mmol, 5 mol%) was added to a solution of the oxazaborolidine,methacrolein (43 muL, 0.5 mmol, 1 equiv), and cyclopentadiene(125 muL, 1.5 mmol, 3 equiv) in CH2Cl2 (2.5 mL) and the mixturewas stirred for 2 h at -78 C. The reaction was quenched with sat. aqNaHCO3 and extracted with Et2O. The combined organic phase waswashed with brine, and dried (Na2SO4). After filtration and removal ofsolvent, the crude product was purified by column chromatography(silica gel, pentane/Et2O 9:1) to afford the Diels-Alder adduct (67 mg,98%) as a colorless oil. The enantioselectivity was determined to be84% ee by GC analysis after conversion into the chiral acetal by(2R,4R)-pentane-2,4-diol.GC [ULBON HR-20M (PEG-20M), 100 C]: tR = 24.3 (minor), 26.0 min(major).1H NMR (400 MHz, CDCl3): delta = 9.70 (s, 1 H), 6.31 (dd, J = 2.9, 6.1 Hz, 1H), 6.11 (dd, J = 6.1, 3.0 Hz, 1 H), 2.87 (br s, 1 H), 2.81 (br s, 1 H), 2.22(dd, J = 3.8, 12.0 Hz, 1 H), 1.35-1.42 (m, 1 H), 1.22-1.28 (m, 1 H), 1.00(s, 3 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,80466-51-9, its application will become more common.
Reference:
Article; Shimoda, Yasushi; Yamamoto, Hisashi; Synthesis; vol. 49; 1; (2017); p. 175 – 180;,
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