Preparation method of bridge ring compound
A compound and bridged ring technology is applied in the field of the preparation of bridged ring compounds, which can solve the problem that raw materials are not easy to obtain product yield, etc., and achieve the effects of low raw material cost, high yield and simple post-processing operation.
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[0025]As analyzed in the background technology of the present application, the raw materials used in the synthesis of bridged ring compounds in the prior art are not easy to obtain and the yield of products is low. In order to solve this problem, the application provides a preparation method of bridged ring compounds. The preparation method includes: step S1, using Boc-L-pyroglutamate methyl ester or Boc-L-pyroglutamate ethyl ester as a substrate, and subjecting the substrate to a reduction-ether formation reaction to obtain the first compound having the structural formula A An intermediate; step S2, subjecting the first intermediate to a substitution reaction to obtain a second intermediate with structural formula B; step S3, subjecting the second intermediate to a hydrolysis reaction to obtain a third intermediate with structural formula C; step S4 , making the third intermediate undergo a ring closure reaction to obtain a fourth intermediate with structural formula D; and st...
Embodiment 1
[0045]Step S1, add tetrahydrofuran (10vol.) and 503.0g Boc-L-pyroglutamic acid methyl ester (1.0equiv.) into the four-necked reaction flask, lower the temperature to -70~-78°C, and at this temperature Slowly add lithium triethylborohydride (1.2 equiv.) dropwise, continue to stir at -70~78°C for 60 minutes after the dropwise addition, and use TLC and HPLC to monitor the completion of the reaction to obtain a reduced product system. Slowly add saturated aqueous sodium bicarbonate solution dropwise to the four-neck reaction flask at 78°C to quench the reaction. After the quenching is completed, place the obtained reduced product system at 0-5° C. and continue to stir for 30 minutes, then slowly raise the temperature of the system to 20-25° C. Add methyl tert-butyl ether to the reduction product system for extraction and liquid separation (10 vol.*3, 10 vol. of extractant for each time, three times in total). Combine the organic phases obtained by extraction and wash the organic ...
Embodiment 2
[0061] Step S1, add tetrahydrofuran (10vol.) and 503.0g Boc-L-pyroglutamic acid methyl ester (1.0equiv.) into the four-necked reaction flask, lower the temperature to -70~-78°C, and at this temperature Lithium triethylborohydride (1.0 equiv.) was slowly added dropwise. The rest was the same as in Example 1 to obtain 396.7 g of a colorless oily compound (ie reduction-etherification product), with a total yield of 77%.
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