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Preparation method of 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid

A technology of benzylpyrrolidine and benzyl, applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as being unsuitable for synthesis, and achieve the effects of enhanced possibility of industrialization and simplified operation

Active Publication Date: 2017-07-11
CHEMSHUTTLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The other two methods of generating carbene and then reacting with ethylenic bonds to form a ring are not suitable for the synthesis of this compound

Method used

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  • Preparation method of 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid

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Experimental program
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Effect test

Embodiment 1

[0027] A kind of preparation method of 5-benzyl-5-N heterospiro[2.4]heptane-1-carboxylic acid, described preparation method comprises the steps:

[0028] (1) 1-benzyl-3-hydroxypyrrolidine is produced through Sven oxidation reaction to obtain 1-benzyl-3-carbonylpyrrolidine;

[0029] ①Add 12.50g of oxalyl chloride dropwise to 70mL of dichloromethane, stir, cool to below -65°C, add dropwise 5.0g of DMSO in DCM, keep the temperature at -65°C, and stir for half an hour after the addition;

[0030] ② Add 8.80g of 1-benzyl-3-hydroxypyrrolidine DCM solution dropwise, keep at -65°C, after the addition is complete, TCL tracking monitoring, react for 2h, after the reaction is complete, add Et3N dropwise at -65°C, temperature Control at -65°C, after the addition is complete, stir for half an hour;

[0031] ③Then the temperature was raised to 0°C, water was added dropwise, the solution changed from a suspension to a clear liquid, and the layers were separated, the organic layer was washed...

Embodiment 2

[0040] A kind of preparation method of 5-benzyl-5-N heterospiro[2.4]heptane-1-carboxylic acid, described preparation method comprises the steps:

[0041] (1) 1-benzyl-3-hydroxypyrrolidine is produced through Sven oxidation reaction to obtain 1-benzyl-3-carbonylpyrrolidine;

[0042] ① Add 6.89g of oxalyl chloride dropwise to 70mL of dichloromethane, stir, cool to below -65°C, add dropwise 4.25g of DMSO in DCM, keep the temperature at -65°C, and stir for half an hour after the addition;

[0043] ② Add 11g of 1-benzyl-3-hydroxypyrrolidine DCM solution dropwise, keep at -65°C, after the addition is complete, TCL tracking monitoring, react for 2h, after the reaction is complete, add Et3N dropwise at -65°C, temperature control At -65°C, after the addition is complete, stir for half an hour;

[0044]③Then the temperature was raised to 0°C, water was added dropwise, the solution became a clear solution from a suspension, the layers were separated, the organic layer was washed with br...

Embodiment 3

[0052] A kind of preparation method of 5-benzyl-5-N heterospiro[2.4]heptane-1-carboxylic acid, described preparation method comprises the steps:

[0053] (1) 1-benzyl-3-hydroxypyrrolidine is produced through Sven oxidation reaction to obtain 1-benzyl-3-carbonylpyrrolidine;

[0054] ①Add 25.00g of oxalyl chloride dropwise to 70mL of dichloromethane, stir, cool to below -65°C, add dropwise 10.00g of DMSO in DCM, keep the temperature at -65°C, and stir for half an hour after the addition;

[0055] ② Add 8.80g of 1-benzyl-3-hydroxypyrrolidine DCM solution dropwise, keep at -65°C, after the addition is complete, TCL tracking monitoring, react for 2h, after the reaction is complete, add Et3N dropwise at -65°C, temperature Control at -65°C, after the addition is complete, stir for half an hour;

[0056] ③Then the temperature was raised to 0°C, water was added dropwise, the solution changed from a suspension to a clear liquid, and the layers were separated, the organic layer was wash...

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Abstract

The invention discloses a preparation method of 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid. The preparation method comprises that through a series of Swern oxidation reaction, Wittig reaction, sulfur ylide reaction and hydrolysis reaction, 5-benzyl-5-N spiro[2. 4]heptane-1-carboxylic acid is prepared from 1-benzyl-3-hydroxypyrrolidine. The preparation method utilizes a reaction of the double bond and the sulfur ylide to produce the ternary ring, utilizes cheap and easily available raw materials, has mild conditions, utilizes a simple operation way and greatly improves the possibility of industrialization.

Description

technical field [0001] The present invention relates to the technical field of synthesizing pharmaceutical intermediates, in particular to a method of preparing 5-benzyl-5-pyrrolidine from 1-benzyl-3-hydroxypyrrolidine through the processes of Sven oxidation, Wittig reaction, ring formation and hydrolysis. -N heterospiro[2.4]heptane-1-carboxylic acid method. Background technique [0002] Three-membered ring compounds are widely used in pharmaceutical intermediates. Since the bond angle of the three-membered ring is 60° and the tension is relatively high, the three-membered ring cannot be formed under high temperature or hydrogenation conditions during the reaction. In the laboratory, the reaction of carbene and ethylenic bond is usually used to form a three-membered ring. There are three methods for the generation of carbene, 1) the reaction of haloform compound and strong base; 2) the reaction of diazo compound with rhodium or copper catalyst; 3 ) Diiodomethane reacts with...

Claims

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Application Information

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IPC IPC(8): C07D209/54
CPCC07D209/54
Inventor 苟刚明
Owner CHEMSHUTTLE
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