Method for synthesizing N-tert-butoxycarbonyl group-3-hydroxy azetidine
A technology of tert-butoxycarbonyl and heterocyclobutane, which is applied in the field of synthesis of N-Boc-3-hydroxyazetidine, can solve the problems of messy reaction process and difficult purification of reaction products, and meet the requirements of production equipment. High, easy handling and short production times
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example 1
[0012] Synthesis of N-Boc-3-hydroxyazetidine
[0013] 3-Hydroxy-N-benzhydrylazetidine (50 g, 0.2 mol) was dissolved in 500 ml methanol. Add 0.5g of palladium hydroxide and 50g of ammonium formate, replace with nitrogen and pass in hydrogen for three times to stabilize the pressure in the kettle at 45-55psi, and stir at 50-55°C for 4-5 hours. After the reaction of 3-hydroxy-N-benzhydrylazetidine was detected by HPLC, it was filtered through a Buchner funnel, and the filtrate was concentrated at 40° C. to remove 300 ml of methanol, and petroleum ether was added for extraction (100 ml*5). After the diphenylmethane was extracted by TLC, sodium bicarbonate (57g, 0.4mol) was added, stirred for 5-10min, Boc (55g, 0.25mol) was slowly added dropwise, and after stirring at room temperature for 10 hours, the reaction solution was heated at 40°C Concentrate to dryness below. Then add dichloromethane (120ml), N,N-diethylethylenediamine (29g, 0.25mol) and stir for 1 hour, wash three tim...
example 2
[0017] Synthesis of N-Boc-3-hydroxyazetidine
[0018] 3-Hydroxy-N-benzhydrylazetidine (50 g, 0.2 mol) was dissolved in 500 ml methanol. Add 0.5g of palladium hydroxide and 50g of ammonium formate, replace with nitrogen and pass in hydrogen for three times to stabilize the pressure in the kettle at 45-55psi, and stir at 50-55°C for 4-5 hours. After the reaction of 3-hydroxy-N-benzylazetidine was detected by HPLC, it was filtered through a Buchner funnel, and the filtrate was concentrated at 40° C. to remove 200 ml of methanol, and petroleum ether was added for extraction (100 ml*5). After the diphenylmethane was extracted by TLC, sodium bicarbonate (57g, 0.4mol) was added, stirred for 5-10min, Boc (55g, 0.25mol) was slowly added dropwise, and after stirring at room temperature for 10 hours, the reaction solution was heated at 40°C Concentrate to dryness below. Then add dichloromethane (120ml), N,N-diethylethylenediamine (29g, 0.25mol) and stir for 1 hour, wash three times w...
example 3
[0022] Synthesis of N-Boc-3-hydroxyazetidine
[0023] 3-Hydroxy-N-benzhydrylazetidine (50 g, 0.2 mol) was dissolved in 5 L of methanol. Add 0.5g of palladium hydroxide and 50g of ammonium formate, replace with nitrogen and pass in hydrogen for three times to stabilize the pressure in the kettle at 40-45psi, and stir at 50-55°C for 4-5 hours. After the reaction of 3-hydroxy-N-benzhydrylazetidine was detected by HPLC, it was filtered through a Buchner funnel, and the filtrate was concentrated at 40° C. to remove 300 ml of methanol, and petroleum ether was added for extraction (100 ml*5). After the diphenylmethane was extracted by TLC, sodium bicarbonate (57g, 0.4mol) was added, stirred for 5-10min, Boc (55g, 0.25mol) was slowly added dropwise, and after stirring at room temperature for 12 hours, the reaction solution was heated at 40°C Concentrate to dryness below. Then add dichloromethane (120ml), N,N-diethylethylenediamine (29g, 0.25mol) and stir for 1 hour, wash three tim...
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