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Preparation method for tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid

A technology of tert-butyldioxy and diazabicyclo, which is applied in the field of preparation of tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid , which can solve the problems of difficult reaction control, low yield, inconvenient experimental operation, etc., and achieve the effect of reasonable reaction process design and saving synthesis cost.

Active Publication Date: 2016-02-03
SHANGHAI SYNTHEALL PHARM CO LTD +2
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Problems solved by technology

It mainly solves technical problems such as low yield, uneasy control of reaction and inconvenient experimental operation in the existing synthesis process

Method used

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  • Preparation method for tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid
  • Preparation method for tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid
  • Preparation method for tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid

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[0011] Synthesis of methyl tert-butoxycarbonyl pyroglutamate

[0012]

[0013] Add 218 grams of BOC anhydride to 143 grams of methyl tert-butoxycarbonyl pyroglutamate and 122 grams of 4-dimethylaminopyridine in 500 milliliters of dichloromethane solution, and stir at room temperature for 12 hours. After the reaction, the reaction solution was washed twice with dilute hydrochloric acid and once with saturated brine, and dried to obtain the product with a yield of 75%.

[0014] 1 H-NMR (CDCl3): 4.59(s, 1H), 3.7(s, 3H), 2.6(m, 1H), 2.5(m, 1H), 2.3(m, 1H), 2.0(m, 1H), 1.49 (s, 9H).

[0015] tert-Butyl-5-hydroxypyrrolidine-2-oic acid methyl ester

[0016]

[0017] Add 5g of sodium triethylborohydride into an ethanol solution in which 10 grams of methyl tert-butoxycarbonyl pyroglutamate is dissolved at zero degrees Celsius, react for 2 hours, add saturated aqueous sodium bicarbonate solution at zero degrees Celsius, Warm up to room temperature, add 2 ml of hydrogen per...

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Abstract

The invention relates to a preparation method for tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid, and mainly solves the technical problems that in an existing synthetic process, the yield is low, the reaction is not easy to control, the experimental operation is inconvenient and the like. By taking t-butyloxycarboryl methyl pyroglutamate as an initial raw material, the tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid is prepared by five-step reactions. The tert-butyl dioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid obtained by the method provided by the invention is a useful intermediate or an intermediate product for synthesis of multiple drugs.

Description

technical field [0001] The present invention relates to a synthesis method of tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid (CAS: 417727-40-3). Background technique [0002] Tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid and related derivatives have important applications in medicinal chemistry and organic synthesis, and have excellent prospects. At present, there are few reports on the synthesis of tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid in the literature. Its synthetic route (PCTint.Appl., 2002032901) is as follows: [0003] [0004] Using the difficult-to-obtain imino ether as a raw material, and then reacting with nitromethane, the next step product can hardly be obtained. The tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid disclosed in this document is very difficult to synthesize. [0005] Therefore, it is of great significance to develop a synthetic method with easy-to-obtain raw material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08
Inventor 唐小伍毛延军陈琳琳周强钱国磊李红杨彩民张同心孙伟于凌波徐学芹何振民马汝建陈民章傅小勇王文贵
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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