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Preparation method of 4-amino-tetrahydro-2-pyran-4-carboxylic acid

A technology of tetrahydropyranone and tetrahydrofuran, applied in directions such as organic chemistry, can solve the problems of complicated post-processing, low yield, and difficulty in industrialized production, and achieve the effects of easy purification, simple operation process, and reduced waste

Pending Publication Date: 2019-06-28
上海卡洛化学有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] But the synthetic method yield of above-mentioned existing literature is lower, and aftertreatment is complicated, is difficult for suitability for industrialized production, therefore needs to propose a kind of new method for preparing 4-aminotetrahydro-2-pyran-4-carboxylic acid

Method used

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  • Preparation method of 4-amino-tetrahydro-2-pyran-4-carboxylic acid
  • Preparation method of 4-amino-tetrahydro-2-pyran-4-carboxylic acid
  • Preparation method of 4-amino-tetrahydro-2-pyran-4-carboxylic acid

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Effect test

Embodiment 1

[0049] Embodiment 1: a kind of preparation method of 4-aminotetrahydro-2-pyran-4-carboxylic acid comprises the following steps:

[0050] Step 1. Add 100g of tetrahydropyrone into 500mL of deionized water and 500mL of ethanol, then add 247g of ammonium carbonate, add 89g of sodium cyanide, heat to 60°C for 3 hours, cool to 5°C, and filter Dry under vacuum at 70°C for 4 hours, wash the filter cake twice with ice water at -1.5°C to obtain a white solid, and dry to obtain 165g of Intermediate 1.

[0051] 1H NMR(DMSO-d6):10.35(br s,1 H),8.59(s,1 H),3.76(dt,2H),3.55(td,2H),1.79(ddd,2H),1.43- 1.41 (m, 2 H), according to the inspection data of proton nuclear magnetic resonance spectrum, it can be known that the chemical structural formula of the above-mentioned intermediate one is: Simultaneously, the chemical reaction equation of step 1 is as figure 2 shown.

[0052] Step 2: Add 165g of intermediate 1 to 2L of DMF, then add 5g of DMAP, dropwise add 465g of di-tert-butyl dicarbon...

Embodiment 2

[0057] Embodiment 2: a kind of preparation method of 4-aminotetrahydro-2-pyran-4-carboxylic acid comprises the following steps:

[0058] Step 1. Add 100 g of tetrahydropyrone into 800 ml of water and 800 ml of ethanol, then add 200 g of ammonium carbonate and 50 g of sodium cyanide, heat to 65 ° C for 4 hours, and filter with a suction filter funnel to obtain The filter cake was washed twice with ice water at about 1.5°C to obtain a white solid, which was dried under vacuum at 40°C for 4 hours to obtain 160 g of Intermediate 1.

[0059] Step 2: Add 160g of intermediate 1 into 1.6L of DMF, then add 5g of DMAP, dropwise add 450g of di-tert-butyl dicarbonate, heat up to 90°C, react for 18h, pour into water and stir for 2.5h, filter It was dried under vacuum at 40°C for 5 hours to obtain 310 g of Intermediate II.

[0060] Step 3: Add 310g of intermediate 2 into 1.085L of tetrahydrofuran, then add 775ml of 40wt% sodium hydroxide solution, heat to reflux at 50°C for 6h, distill off...

Embodiment 3

[0061] Embodiment 3: a kind of preparation method of 4-aminotetrahydro-2-pyran-4-carboxylic acid comprises the following steps:

[0062] Step 1. Add 100 g of tetrahydropyrone into 600 ml of water and 600 ml of ethanol, then add 300 g of ammonium carbonate and 120 g of sodium cyanide, heat to 70 ° C for 3 hours, and filter with a suction filter funnel to obtain The filter cake was washed three times with ice water at 0°C to obtain a white solid, which was dried under vacuum at 60°C for 5 hours to obtain 170 g of Intermediate 1.

[0063] Step 2: Add 170g of intermediate 1 into 2.55L of DMF, then add 5g of DMAP, dropwise add 475g of di-tert-butyl dicarbonate, heat up to 100°C, react for 20h, pour into water and stir for 2h, filter and put in It was dried under vacuum at 60°C for 6 hours to obtain 300 g of intermediate 2.

[0064] Step 3: Add 300g of intermediate 2 into 1.86L of tetrahydrofuran, then add 750ml of 60wt% sodium hydroxide solution, heat and reflux at 60°C for 6h, di...

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Abstract

The present invention discloses a preparation method of 4-amino amino-tetrahydro-2-pyran-4-carboxylic acid, and belongs to chemical intermediates. The preparation method is characterized by includingthe steps of 1, adding tetrahydro-pyranone to water and alcohol, adding ammonium carbonate and sodium cyanide, heating to 60-70 DEG C for reaction for 3-4 hours, cooling to 5-10 DEG C, and obtaining an intermediate I after being filtered and dried; 2, adding the intermediate I to DMF, adding DMAP, then adding di-tert-butyl dicarbonate in a dropwise manner, heating to 80-100 DEG C, stirring for 2-3hours after being subjected to reaction for 16-20 hours, and filtering to obtain an intermediate II; and 3, adding the intermediate II to tetrahydrofuran, adding 40-60% of sodium hydroxide solution by weight, carrying out heating reflux for 5-6 hours, distilling off the tetrahydrofuran, precipitating solid through regulation of pH value to 2-4 by using hydrochloric acid, and obtaining the 4-aminoamino-tetrahydro-2-pyran-4-carboxylic acid after being filtered and dried.

Description

technical field [0001] The invention belongs to a chemical intermediate, more specifically, it relates to a preparation method of 4-aminotetrahydro-2-pyran-4-carboxylic acid. Background technique [0002] 4-aminotetrahydro-2-pyran-4-carboxylic acid, the molecular formula is: C 6 h 11 NO 3 , CAS number is 39124-20-4, its English name is: 4-aminooxane-4-carboxylic acid, its chemical structure is: There are currently two conventional synthesis methods: [0003] 1. References: Boddaert, Thomas; Sola, Jordi; Helliwell, Madeleine; Clayden, Jonathan Chemical Communications, 2012, vol.48, #28p.3397-3399 is the 8 with CAS number 39124-19-1 -Oxa-1,3-diazaspiro[4.5]decane-2,4-dione is synthesized from raw materials, and its reaction equation is: [0004] [0005] 2. References: Elf Sanofi Patent: US5270317 A1, 1993; the document of US 5270317 A is synthesized by using 2-cyclopentylacetic acid as the main raw material, and its reaction equation is: [0006] [0007] However...

Claims

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Application Information

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IPC IPC(8): C07D309/14
Inventor 谭君成张银兰
Owner 上海卡洛化学有限公司
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