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A kind of preparation method of β-amino acetal
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A technology of amino acetal and amine acetal, which is applied in the field of preparation of β-amino acetal, can solve the problems of complex operation, poor substrate adaptability, low yield, etc., and achieve simple synthesis process, mild reaction conditions, and reaction selection good sex effect
Inactive Publication Date: 2016-09-07
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology
[0004] Existing methods are not easy to produce on a large scale due to various shortcomings, for example: method 1, the preparation of nitroacetal needs to use formyl acetal as a raw material, and requires a large amount of alkali at the same time, during the addition reaction process Need again a large amount of organometallic reagents, atom economy is poor, operation is complicated, and step is long; Method two, β-bromopropyl acetal is difficult for preparation, needs to use a large amount of alkali simultaneously, and reaction selectivity is poor, and yield is low; Method three, It is necessary to use aromatic aldehydes to form imines with amines first. The substrate adaptability is poor, and it needs to be carried out at low temperature, and the operation is complicated. At the same time, the obtained aminoaldehydes have poor stability and are not easy to store
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Embodiment 1
[0028] The preparation of embodiment 1, β-amino acetal 4a
[0029]
[0030] n-Butyl vinyl ether 1a (80 mg, 0.8 mmol), Pd(Xantphos)Cl 2 (15.1 mg, 5mol %, 0.02 mmol), amine acetal 2a (164.2 mg, 0.4 mmol) and isopropanol (1.5 mL) were added to the reaction flask, 110 o The reaction was carried out under the condition of C for 12 hours, and the pure β-amino acetal 4a was obtained by column chromatography (using silica gel column; eluent: petroleumether / ethyl acetate=100 / 1). The product was a colorless liquid with a yield of 74%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.30-7.35 (m, 4H), 7.22-7.29 (m, 4H), 7.19-7.21 (m, 2H), 4.55 (t, J = 5.6 Hz, 1H),3.71-3.77 (m, 1H), 3.54 (s, 4H), 3.39-3.44 (m, 1H), 3.23-3.29 (m, 1H), 2.46-2.56 (m, 2H), 1.74-1.86 (m, 2H), 1.38-1.45 (m, 2H ), 1.23-1.32 (m, 2H), 1.13(d, J = 6.0 Hz, 3H), 1.00 (d, J = 6.0 Hz, 3H), 0.87 (t, J = 7.2 Hz, 3H); 13 CNMR (100 MHz, CDCl 3 for C 24 h 36 NO 2 [M+H]: 370.2741, found: 370.2747.
Embodiment 2
[0031] The preparation of embodiment 2, β-amino acetal 4a
[0032]
[0033] n-Butyl vinyl ether 1a (80 mg, 0.8 mmol), Pd(Xantphos)(CH 3 EN) 2 (OTf) 2 (21.3 mg, 5 mol %, 0.02 mmol), amine acetal 2a (164.2 mg, 0.4 mmol) and isopropanol (1.5 mL) were added to the reaction flask, 110 oThe reaction was carried out under the condition of C for 12 hours, and the pure β-amino acetal 4a was obtained by column chromatography (using silica gel column; eluent: petroleumether / ethyl acetate=100 / 1). The product was a colorless liquid with a yield of 84%.
Embodiment 3
[0034] The preparation of embodiment 3, β-amino acetal 4a
[0035]
[0036] n-Butyl vinyl ether 1a (80 mg, 0.8 mmol), Pd(Xantphos)(CH 3 EN) 2 (OTf) 2 (21.3 mg, 5 mol %, 0.02 mmol), amine acetal 2a (164.2 mg, 0.4 mmol), isopropanol (240 mg, 4mmol) and toluene (1.5 mL) were added to the reaction flask, 110 o The reaction was carried out under the condition of C for 12 hours, and the pure β-amino acetal 4a was obtained by column chromatography (using silica gel column; eluent: petroleumether / ethyl acetate=100 / 1). The product is a colorless liquid with a yield of 85%.
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Abstract
The invention discloses a preparation method of beta-amino acetal, and belongs to the organic chemical synthesis technical field. The method comprises that a metal is taken as a catalyst, in an organic solvent, vinyl ether undergoes a reaction with alcohol, amine and aldehyde or with alcohol and amine acetal at the temperature of 25-140 DEG C and a one-pot reaction is carried out at one step for efficiently preparing beta-amino acetal. The reaction raw materials and the catalyst are cheap and easy to get, and the synthetic process is simple; the reaction conditions are mild, the yield is high, and industrialization is easy to implement; the reaction raw materials and the catalyst are clean and non-toxic, and have little pollution to the environment; and the product can be further transformed to synthesize various non-natural beta-amino acids and beta-amino alcohols.
Description
technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of β-amino acetal. Background technique [0002] β-Aminoaldehyde is an important pharmacophore and an important intermediate in the synthesis of peptides, pesticides, medicines and natural products. β-amino acetal can be considered as the equivalent of amino aldehyde, and β-amino aldehyde can be synthesized by hydrolysis and deprotection. The preparation of β-amino aldehydes can also be synthesized by first reducing the corresponding β-amino acids to β-amino alcohols, and then through selective oxidation. Synthesis of β-amino aldehydes through amino acid reduction and oxidation is not only complicated in process, but also requires a large amount of reducing agents and oxidants, low atom economy and high cost, and because common natural amino acids are generally α-amino acids, β - The source of amino acids is also very limited....
Claims
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