Synthetic method of 3-hydroxyazetidine hydrochloride
A technology of tetracyclobutane and synthesis method, which is applied in the new synthesis field of 3-hydroxyazetidine hydrochloride, can solve the problems of disordered reaction process, expensive raw materials, difficult purification of reaction products, etc. Short, cheap raw materials, easy to operate
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Embodiment 1
[0017] 1) Cyclization reaction:
[0018] Under nitrogen protection, tert-butylamine (100.0 g, 1.37 mol), isopropanol (500.0 mL) and epichlorohydrin (115.0 g, 1.24 mol) were added into a 1.0 L three-necked reaction flask. The reaction was then stirred at room temperature for 24-48 hours. Sodium bicarbonate (315.2 g, 3.75 mol) was added. Then the temperature was raised to reflux, and the reaction was stirred for 3-6 hours. Cooling, filtration, desolvation under reduced pressure obtains N-tert-butyl-3-hydroxyl azetidine (formula 3 ) (112.8 g, 0.87 mol, purity: 99.0%, yield 70.0%).
[0019] 2) Acetyl reaction:
[0020] Under nitrogen protection, 108.0 mL of acetic anhydride was added to a 500.0 mL three-necked reaction flask, and then the compound of formula 3 (21.7 g, 0.17 mol) was added in batches. Zinc chloride (10.0 g, 0.075 mol) was then added. React at 125-130°C for 3-10 hours. De-acetic anhydride under reduced pressure obtains N-acetyl group-3-acetoxyl azetidine (for...
Embodiment 2
[0024] 1) Cyclization reaction:
[0025] Under nitrogen protection, tert-butylamine (108.8 g, 1.49 mol), isopropanol (500.0 mL) and epichlorohydrin (115.0 g, 1.24 mol) were added into a 1.0 L three-necked reaction flask. The reaction was then stirred at room temperature for 24-48 hours. Add sodium bicarbonate (315.2 g, 3.75 mol). Then the temperature was raised to reflux state, and the reaction was stirred for 3-6 hours. Cool down to room temperature, filter, and desolventize under reduced pressure. After drying, N-tert-butyl-3-hydroxyazetidine (formula 3 ) （ 115.0 g, 0.89 mol, purity: 99.0%, yield 71.4%).
[0026] 2) Acetyl reaction:
[0027] Under nitrogen protection, 108.0 mL of acetic anhydride was added to a 500.0 mL three-necked reaction flask, and then the compound of formula 3 (21.7 g, 0.17 mol) was added in batches. Additional zinc chloride (8.0 g, 0.060 mol) was added. Then react at 130-135°C for 3-10 hours. Decompression removes acetic anhydride, obt...
Embodiment 3
[0031] 1) Cyclization reaction:
[0032] Under nitrogen protection, tert-butylamine (127.0 g, 1.74 mol), isopropanol (500.0 mL) and epichlorohydrin (115.0 g, 1.24 mol) were added into a 1.0 L three-necked reaction flask. The reaction was then stirred at room temperature for 24-48 hours. Sodium bicarbonate (416.9 g, 4.96 mol) was added. Then the temperature was raised to reflux state, and the reaction was stirred for 3-6 hours. Cool down to room temperature, filter, and desolventize under reduced pressure. After drying, N-tert-butyl-3-hydroxyazetidine (formula 3 ) (113.0 g, 0.87 mol, purity: 99.5%, yield 70.2%).
[0033] 2) Acetyl reaction:
[0034] Under nitrogen protection, 108.0 mL of acetic anhydride was added to a 500.0 mL three-necked reaction flask. Then the compound of formula 3 (21.7 g, 0.17 mol) was added in batches, and then zinc chloride (10.0 g, 0.075 mol) was added. React at 135-140°C for about 3-10 hours. Remove acetic anhydride under reduced pressure. A...
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