Synthesis method for 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b] pyridine-6-carboxylic acid
A technology of tert-butoxycarbonyl and octahydrofuran, which is applied in the field of synthesis of 4-(tert-butoxycarbonyl) octahydrofuro[3,2-b]pyridine-6-carboxylic acid, can solve the problem that is not suitable for industrial synthesis Methods and other issues, to achieve the effect of convenient operation, easy reaction, and short route
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Embodiment 1
[0011] Embodiment 1: compound 1 (7.11g, 51.1mmol) was dissolved in ethanol (300mL), and thionyl chloride (36mL) was added dropwise at room temperature, and the reaction was refluxed overnight. TLC (ethyl acetate=1, R f =0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.
[0012] compound 2 Add water (150mL) to the solution, add sodium carbonate (7.33g, 0.307mol) and iodine (9.65g, 0.153mol), and react at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f =0.8) shows that the reaction is complete, and the reaction solution is added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which is filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (9.3g), yield 82%.
[0013] 1 CDCl 3 , δ1.36–1.40(m...
Embodiment 2
[0022] Embodiment 2: compound 1 (71.1g, 511mmol) was dissolved in ethanol (1500mL), and thionyl chloride (360mL) was added dropwise at room temperature, and the reaction was refluxed overnight. TLC (ethyl acetate=1, R f =0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.
[0023] compound 2 Add water (1500mL) to the solution, add sodium carbonate (73.3g, 3.07mol) and iodine (96.5g, 1.53mol), and react at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f =0.8) shows that the reaction is complete, and the reaction solution is added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which is filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (93.3g), yield 82%.
[0024] 1 CDCl 3 , δ1.36–1.40(...
Embodiment 3
[0033] Embodiment 3: compound 1 (711g, 9.11mol) was dissolved in ethanol (5L), and thionyl chloride (3.6L) was added dropwise at room temperature, and the reaction was refluxed overnight. TLC (ethyl acetate=1, R f =0.8) shows that the reaction is complete, the reaction mixture is spin-dried under reduced pressure, and the residue is added to a saturated aqueous solution of sodium carbonate to make pH=7 to obtain the compound 2 used directly in the next step.
[0034] compound 2 Add water (15L) to the solution, add sodium carbonate (733g, 30.7mol) and iodine (965g, 15.3mol), and react at room temperature for 2 hours. TLC (petroleum ether: ethyl acetate volume ratio=1 / 1, R f =0.8) shows that the reaction is complete, and the reaction solution is added with 1N hydrochloric acid to make the pH=7 to precipitate a solid, which is filtered and spin-dried under reduced pressure to obtain a yellow solid compound 3 (925g), yield 82.5%.
[0035] 1 CDCl 3 , δ1.36–1.40(m,3H)3.91(...
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