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A kind of preparation method of tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

A technology of diazabicyclo and tert-butyl carboxylate, which is applied in the direction of organic chemistry, can solve the problems of uneasy control of the reaction, low yield, inconvenient experimental operation, etc., and achieve the goal of reasonable reaction process design and cost-saving synthesis Effect

Active Publication Date: 2019-01-08
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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  • A kind of preparation method of tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate
  • A kind of preparation method of tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate
  • A kind of preparation method of tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

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[0011] Synthesis of methyl tert-butoxycarbonyl pyroglutamate

[0012]

[0013] 218 g of BOC anhydride was added to 143 g of methyl tert-butoxycarbonyl pyroglutamate and 122 g of 4-dimethylaminopyridine in 500 ml of dichloromethane solution, and the reaction was stirred 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] Methyl tert-butoxycarbonyl-5-hydroxypyrrolidine-2-carboxylate

[0016]

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

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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-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (CAS: 417727-40-3). Background technique [0002] tert-butyl 2-oxo-3,8-diazabicyclo[3.2.1]octane-8-carboxylate and related derivatives have important applications in medicinal chemistry and organic synthesis, and have excellent prospects. At present, there are few reports on the synthetic methods of tert-butyldioxy-3,8-diazabicyclo[3.2.1]octane in the literature. Its synthetic route (PCT int.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 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 materials, convenient operation, easy-to-...

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Application Information

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Patent Type & Authority Patents(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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