Saxagliptin midbody preparing method
A technology of intermediates and compounds, applied in the field of preparation of pharmaceutical intermediates, can solve the problems of cumbersome post-processing, poor chiral selectivity, large amount of solvent, etc., and achieve the effects of easy control of operating conditions, stable activity, and simple preparation
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[0038] The invention discloses a preparation method of a saxagliptin intermediate, which relates to the technical field of preparation of heterocyclic compounds with 1 heterocycle, 3 chiral centers, and amide groups directly connected to ring carbon atoms. Compound of formula VIII. The method comprises the following steps: using (R)-5-hydroxypyrrole-2-one as a raw material, and using benzyl alcohol as a solvent, dehydrating at 70-80°C to obtain 5-benzylhydroxypyrrole-2-one; , reduction, dehydration, cyclopropanation, to generate a compound of formula IV, followed by debenzylation, methylsulfonyl, cyano, and finally hydrolysis to obtain (1S, 3S, 5S)-3-(aminocarbonyl)-2-aza tert-butyl bicyclo[3.1.0]hexane-2-carboxylate.
[0039] The reaction formula is as follows:
[0040]
[0041] The raw materials used in the method of the invention are easy to prepare, the operating conditions are easy to control, the reaction yield is high, there is no pollution, the corresponding isomer ...
Embodiment 1
[0046] Put 30g (R)-5-hydroxypyrrol-2-one, 312g benzyl alcohol, and 2ml hydrochloric acid into the reaction bottle, heat to 70-80°C, keep stirring for 8 hours, check that the reaction of raw materials is complete, cool down to 15-20°C, and filter , the filter cake was rinsed with 10ml of ethyl acetate, and dried to obtain 49.9g of compound I, with a yield of 88% and a melting point of 80-82°C.
Embodiment 2
[0048] Put 10g (R)-5-hydroxypyrrol-2-one, 134g benzyl alcohol, and 0.8ml hydrochloric acid into the reaction bottle, heat to 50-60°C, keep stirring for 10h, check that the reaction of raw materials is complete, and cool down to 15-20°C, After filtering, the filter cake was rinsed with 5ml of ethyl acetate, and dried to obtain 19.5g of compound I, with a yield of 86% and a melting point of 80-82°C.
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