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Synthesis method of (6S,7S)-9-t-butyloxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane

A technology of tert-butoxycarbonyl and trifluoromethyl, applied in (6S,7S)-9-tert-butoxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]-10 In the field of synthesis of alkane, it can solve the problems of no suitable industrial synthesis method, and achieve the effect of reasonable reaction process design, easy reaction and short route

Active Publication Date: 2017-06-13
SHANGHAI SYNTHEALL PHARM CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Synthesis method of (6S,7S)-9-t-butyloxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane
  • Synthesis method of (6S,7S)-9-t-butyloxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane
  • Synthesis method of (6S,7S)-9-t-butyloxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane

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Experimental program
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Embodiment 1

[0012] Example 1: Compound 1 (5 g, 0.022 mol) was dissolved in dichloromethane (50 mL), then oxalyl chloride (5.63 g, 0.044 mol) was added dropwise at 20°C, and stirred at room temperature for 1 hour. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1, R f =0.7) shows that the reaction is complete. The reaction solution was concentrated to remove dichloromethane and oxalyl chloride. The concentrate was dissolved in dichloromethane (50 mL), then methanol (10 mL) was added dropwise at 0°C, and stirred at room temperature for 1 hour. The reaction solution was concentrated to remove dichloromethane and methanol to obtain compound 2 (5.3 g), yield: 100%.

[0013] Compound 2 (5.3g, 0.022mol) and concentrated hydrochloric acid (0.07g, 0.002mol) were added to the suspension of Pd / C (2g) / methanol (100mL), hydrogen gas was exchanged 3 times, 50 degrees Celsius, 50psi stirring reaction 16 hours. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1, R f =0) shows that the reaction is...

Embodiment 2

[0020] Compound 1 (47g, 0.208mol) was dissolved in dichloromethane (500mL), then oxalyl chloride (52.9g, 0.416mol) was added dropwise at 20°C, and stirred at room temperature for 1 hour. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1, R f =0.7) shows that the reaction is complete. The reaction solution was concentrated to remove dichloromethane and oxalyl chloride. The concentrate was dissolved in dichloromethane (200 mL), then methanol (50 mL) was added dropwise at 0°C, and stirred at room temperature for 1 hour. The reaction solution was concentrated to remove dichloromethane and methanol to obtain compound 2 (49.9 g), yield: 100%.

[0021] Compound 2 (49.9g, 0.208mol) and concentrated hydrochloric acid (0.75g, 0.02mol) were added to a suspension of Pd / C (20g) / methanol (1000mL), hydrogen gas was exchanged for 3 times, and the reaction was stirred at 50 degrees Celsius and 50psi 16 hours. TLC (petroleum ether / ethyl acetate volume ratio=5 / 1, R f =0) shows that the re...

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Abstract

The invention relates to a synthesis method of (6S,7S)-9-t-butyloxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane, aiming at mainly solving the technical problem that a suitable industrial synthesis method does not exist at present. The synthesis method is divided into six steps as follows: firstly, taking a compound 1 and oxalyl chloride to react to obtain a compound 2; then, hydrogenating by palladium on carbon to generate a compound 3; taking the compound 3 to react with BOC (Butyloxycarbonyl) acid anhydride under an alkaline condition to obtain a compound 4; taking the compound 4 and acrylonitrile to be subjected to alkylation reaction under the action of sodium ethoxide to obtain a compound 5; carrying out reduction and ring closure on the compound 5 under the action of Raney nickel to obtain a compound 6; reducing the compound 6 with borane-dimethylsulfide to obtain a final compound 7, wherein a reaction formula is shown in the description.

Description

technical field [0001] The invention relates to a synthesis method of compound (6S, 7S)-9-tert-butoxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane. Background technique [0002] Compound (6S, 7S)-9-tert-butoxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane (CAS: 1263178-03-5) and related derivatives It is widely used in medicinal chemistry and organic synthesis. At present, there is no report on the industrial synthesis of (6S,7S)-9-tert-butoxycarbonyl-7-(trifluoromethyl)-2,9-diazaspiro[5.5]undecane. 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 the present invention is to develop a kind of (6S, 7S)-9-tert-butoxycarbonyl-7-(trifluoromethyl)-2,9 that has raw material that is easy to get, easy to operate, easy to control, and high yield. - Sy...

Claims

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Application Information

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IPC IPC(8): C07D471/10
CPCC07B2200/07C07D471/10
Inventor 于凌波周强张大为高明飞姚宝元刘雨雷赵红双韩华新李旭东付新雨马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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