These common heterocyclic compound, 335599-07-0, name is Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-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. name: Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate
Production Example 11-2(3-Oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 1 3-Oxa-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester diastereomer 1 (10 g, 64.1 mmol) was dissolved in TIM (100 mL), and to the mixture, was added dropwise a 0.99M toluene (180 mL, 178 mmol) solution of DIBAL while cooling on ice, and stirred at room temperature for one hour. To the reaction mixture, were added a small amount of water and ethyl acetate, and the mixture was filtered with Celite, washed with ethyl acetate, and then the filtrate was distilled off under reduced pressure, and the residue was purified by column chromatography (heptane:ethyl acetate to 75% ethyl acetate) to obtain the title compound (2.6 g, 228 mmol) as a colorless oil.1H-NMR (CDCl3) delta: 1.10 (dt, J=3.6 Hz, 6.8 Hz, 1H), 1.53-1.56 (m, 2H), 3.53 (d, J=6.8 Hz, 2H), 3.70 (d, J=8.0 Hz, 2H), 3.88 (d, J=8.4 Hz, 2H)Production Example 11-3(3-Oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 2 From 3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester diastereomer 2 (5 g, 32.1 mmol), the title compound (2.1 g, 18.4 mmol) was obtained as a colorless oil according to the same procedure as in (3-oxa-bicyclo[3.1.0]hex-6-yl)methanol diastereomer 1.1H-NMR (CDCl3) delta: 1.23 (t, J=3.6 Hz, 1H), 1.80 (d, J=3.6 Hz, 2H), 3.79 (d, J=7.6 Hz, 2H), 3.91 (m, 4H)
The synthetic route of Ethyl 3-oxa-bicyclo[3.1.0]hexane-6-carboxylate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Eisai R&D Management Co., Ltd.; US2011/86882; (2011); A1;,
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