Preparation method of Boc-1-(benzyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate

A diazaspiro, benzyl technology, applied in Boc-1-(benzyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylic acid In the field of ester production, it can solve the problems of no suitable industrial synthesis method, and achieve the effect of reasonable design of reaction process, convenient operation and easy reaction

Inactive Publication Date: 2019-08-30
WUXI APPTEC (TIANJIN) CO LTD
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Mainly solve the technical problem that there is

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  • Preparation method of Boc-1-(benzyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate
  • Preparation method of Boc-1-(benzyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate

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Embodiment 1

[0012] Compound 1 (4.06 kg, 20.38 mol, 1.00 eq ) was dissolved in toluene (35.00 L), then potassium carbonate (5.63 kg, 40.76 mol, 2.00 eq ) and benzylamine (3.28 kg, 30.57 mol, 3.34 L, 1.50 eq ). Then reacted at 60°C for 18 hours, and the nuclear magnetic resonance of the crude product showed that the reaction was complete. The reaction system was cooled to 25°C, filtered, and the filtrate was spin-dried to obtain crude compound 2.

[0013] Compound 2 (5.88 kg, 20.39 mol, 1.00 eq) was dissolved in toluene (40.00 L), then allylmagnesium bromide (1 M, 24.06 L, 1.5 eq) was added dropwise at 0°C, and reacted at 25°C for 18 hours . TLC (petroleum ether / ethyl acetate volume ratio = 3 / 1) showed that the reaction was complete. The reaction solution was quenched by adding saturated ammonium chloride (40 L). Then it was extracted with ethyl acetate (40L*4), the organic phase was washed with brine, dried and concentrated to obtain the crude product. The crude product was separate...

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Abstract

The invention relates to a synthesis method of tert-butoxycarbonyl-1-(benzyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate, and mainly solve the technical problem that no synthesis method suitablefor industrialization exists at present. The method is divided into three steps: the first step, a compound 1 and benzylamine are reacted to obtain a compound 2 in the solvent toluene under the action of potassium carbonate; the second step, the compound 2 and allyl magnesium bromide are reacted to obtain a compound 3 in toluene; and the third step, the compound 3 and iodine are reacted to obtaina final compound 4 in the solvent acetonitrile under the action of sodium bicarbonate. The reaction formula is as shown in the specification.

Description

technical field [0001] The present invention relates to the preparation method of Boc-1-(phenylmethyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate, namely the compound tert-butoxycarbonyl-1 Synthetic method of -(phenylmethyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate. Background technique [0002] The compound tert-butoxycarbonyl-1-(phenylmethyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate (MFCD28390464) and related derivatives in the pharmaceutical It is widely used in chemistry and organic synthesis. At present, there are few reports on the synthesis methods of tert-butoxycarbonyl-1-(phenylmethyl)-3-iodo-[1,8]diazaspiro[4,5]heptane-8-carboxylate. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of this invention is to develop a kind of tert-butoxy...

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Application Information

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IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 刘爽王密杨云龙毛晶陈冬枝汪永生庞洲张宏伟于凌波马汝建
Owner WUXI APPTEC (TIANJIN) CO LTD
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