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Processes for producing tetrahydropyranyl-4 sulfonate and 4-amino tetrapyran compound

A technology of aminotetrahydropyran compound and tetrahydropyranyl, which is applied in the field of producing 4-aminotetrahydropyran compound and producing tetrahydropyranyl-4-sulfonate, and can solve the problem of tetrahydropyran compound Problems such as low yield, low yield, and difficult synthesis

Inactive Publication Date: 2005-03-16
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, tetrahydropyran-4-one is a compound that is relatively difficult to synthesize. It is extremely unstable to alkali, and because it is easy to ring-open to form a polymer, there are certain difficulties in handling. Therefore, no matter which method is used A method, the productive rate of target product 4-aminotetrahydropyran compound is all very low
[0004] On the other hand, a method of reacting 4-chlorotetrahydropyran and ammonia in a reactor at 200° C. is disclosed (J.Org.Chem., 36 , 522(1971)), but its reaction conditions are very strict and there is also the problem of low yield

Method used

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  • Processes for producing tetrahydropyranyl-4 sulfonate and 4-amino tetrapyran compound
  • Processes for producing tetrahydropyranyl-4 sulfonate and 4-amino tetrapyran compound
  • Processes for producing tetrahydropyranyl-4 sulfonate and 4-amino tetrapyran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1.00 g (13.9 mmol) of 3-buten-1-ol and 1.35 g (16.6 mmol) of 37% by weight aqueous formaldehyde (from Wako Junyaku Co. obtained), under a nitrogen atmosphere, 2.66 g (27.7 mmol) of methanesulfonic acid was added dropwise with stirring, and the resulting mixture was reacted at 25° C. for 3 hours. When the reaction was completed, the resulting reaction mixture was analyzed by high-performance liquid chromatography, and it was found that 1.65 g (yield: 66%) of tetrahydropyranyl-4-methanesulfonate had been formed.

Embodiment 2

[0050] In a reaction apparatus similar to Example 1, 1.00 g (13.9 mmol) of 3-buten-1-ol, 0.50 g (15.3 mmol) of 92% by weight paraformaldehyde (obtained from Mitsui Toatsu Chemical Co.) and 5ml of toluene, under a nitrogen atmosphere, 3.99g (41.5mmol) of methanesulfonic acid was added dropwise with stirring, and the resulting mixture was reacted at 25°C for 3 hours. When the reaction was completed, the resulting reaction mixture was analyzed by high-performance liquid chromatography to find that 2.15 g (yield: 86%) of tetrahydropyranyl-4-methanesulfonate had been formed.

Embodiment 3

[0052] Add 1.00g (13.9mmol) 3-buten-1-ol, 0.50g (5.6mmol, calculated as formaldehyde, it is equivalent to 16.8mmol) trioxane and 5ml Toluene, under a nitrogen atmosphere, 2.66 g (27.7 mmol) of methanesulfonic acid was added dropwise with stirring, and the resulting mixture was reacted at 25° C. for 3 hours. When the reaction was completed, the resulting reaction mixture was analyzed by high performance liquid chromatography to find that 2.13 g (yield: 85%) of tetrahydropyranyl-4-methanesulfonate had been produced.

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Abstract

A process for producing a tetrahydropyranyl-4-sulfonate characterized by reacting 3-buten-1-ol, which is easily available, with a formaldehyde compound and an organic sulfonic acid; and a process suitable for the industrial production of a 4-aminotetrahydropyran derivative, by which the derivative can be produced in high yield under mild conditions through a simple procedure.

Description

technical field [0001] The present invention relates to a process for producing tetrahydropyranyl-4-sulfonate and a process for producing 4-aminotetrahydropyran compound from tetrahydropyranyl-4-sulfonate. Tetrahydropyranyl-4-sulfonate is a useful compound, which can introduce tetrahydropyranyl groups into different compounds through sulfonyl substitution reactions, and 4-aminotetrahydropyran compounds are also a A useful compound, which is a synthetic intermediate or raw material for drugs, pesticides and other substances. Background technique [0002] As a process for producing tetrahydropyranyl-4-sulfonate from 3-butene-1 alcohol, there is known a two-step process through tetrahydropyran-4-ol, for example: 3-Butane En-1 alcohol and formaldehyde aqueous solution synthesize tetrahydropyran-4-ol (Chem.Ber., 88 , p.1053 (1955)), then, in the presence of a base, tetrahydropyran-4-alcohol and methanesulfonyl chloride react to synthesize tetrahydropyranyl-4-methanesulfonate, a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/08C07D309/14
CPCC07D309/08C07D309/14
Inventor 原田胜正西野繁荣岛秀好弘津健二西村实
Owner UBE IND LTD
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