A kind of preparation method of 2-(1-(tert-butoxycarbonyl) azetidinyl-3-) cyclopropyl formic acid
An azetidine, cyclopropylcarboxylic acid technology, applied in the direction of organic chemistry and the like, can solve the problems such as no suitable industrial synthesis method, and achieve the effects of avoiding inflammability and explosion, convenient operation and novel reaction
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Embodiment 1
[0010] Example 1: a. Dissolve compound 1 (100 g, 0.5 mol) in tetrahydrofuran (2 L), add sodium hydride (36 g, 1.5 mol) at 10°C to 20°C and stir for 30 minutes, then add methyl iodide (142 g, 1.0 mol) was added dropwise to the reaction system at 5°C to 10°C. The reaction system was stirred at 15°C to 25°C for 16 hours. TLC (petroleum ether / ethyl acetate=1 / 1, volume ratio, the same below) showed that the reaction was complete. The reaction system was poured into ice water (2 L) and extracted with ethyl acetate (1.5 L x 3). The obtained organic phases were combined, washed with saturated brine, dried and filtered, and concentrated under reduced pressure to obtain compound 2 (100 g), with a yield of 95%.
[0011] δ4.328-4.315 (m, 2H), 4.100-4.070 (m, 2H), 3.68 (s, 3H), 3.070-3.050 (m, 1H), 1.380 (s, 9H).
[0012] b. Suspend lithium aluminum hydride (27 g, 0.70 mol) in THF, control the reaction system at -10°C to 0°C, add compound 2 (100 g, 0.47 mol) in tetrahydrofuran (200 mL) ...
Embodiment 2
[0021] Example 2: a. Dissolve compound 1 (500 g, 2.5 mol) in tetrahydrofuran (8 L), add NaH (180 g, 7.5 mol) at 10°C to 20°C and stir for 30 minutes, then MeI (710 g, 5.0 mol) into the reaction system dropwise at 5°C to 10°C. The reaction system was stirred at 15°C to 25°C for 16 hours. TLC (petroleum ether / ethyl acetate = 1 / 1) showed the reaction was complete. The reaction system was poured into ice water (8 L) and extracted with ethyl acetate (4 L x 3). The obtained organic phases were combined, washed with saturated brine, dried and filtered, and concentrated under reduced pressure to obtain compound 2 (500 g), with a yield of 95%.
[0022] δ4.328-4.315 (m, 2H), 4.100-4.070 (m, 2H), 3.68 (s, 3H), 3.070-3.050 (m, 1H), 1.380 (s, 9H).
[0023] b. Suspend lithium aluminum hydride (135 g, 3.5 mol) in tetrahydrofuran, control the reaction system at -10°C to 0°C, add compound 2 (500 g, 2.35 mol) in tetrahydrofuran (800 mL) dropwise to in the reaction system. The reaction was ...
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