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A kind of method that takes halomethyl compound as raw material to prepare deuterated aldehyde

A compound, halomethyl technology, applied in the field of compound preparation, can solve problems such as harsh reaction conditions, limited substrate range, cumbersome multi-step operation, etc., and achieve the effect of simple reaction conditions, simple operation and wide applicability

Active Publication Date: 2021-11-19
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these methods require tedious multi-step operations, expensive deuterated reagents, or harsh reaction conditions
In addition, new methods for the synthesis of deuterated aldehydes have recently been developed, such as Cp 2 Although good progress has been made in the reaction of ZrDCl with tertiary amides, decarboxylation of oxocarboxylic acids, and direct H / D exchange catalyzed by ruthenium, there are still many challenging problems to be solved in the synthesis, especially the High temperature reaction conditions, limited substrate coverage, low availability of reagents, and low deuteration rates limit the practical application of these methods

Method used

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  • A kind of method that takes halomethyl compound as raw material to prepare deuterated aldehyde
  • A kind of method that takes halomethyl compound as raw material to prepare deuterated aldehyde
  • A kind of method that takes halomethyl compound as raw material to prepare deuterated aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of 2-deuterated naphthaldehyde (A1)

[0045] First mix DMSO (3mL) with D 2 O (1 mL) was mixed and stirred for 5 minutes, then 2-naphthylmethyl bromide (0.5 mmol), 4-picoline (2 mmol), potassium phosphate (2 mmol) were added sequentially. The reaction was stirred at room temperature for 10 hours, then 4-dimethylaminonitrosobenzene (1 mmol) was added at room temperature. The mixed reaction solution was continued to react at room temperature for 4 hours, then slowly added dropwise 12 mL of 3M hydrochloric acid solution under ice-bath conditions, then continued to stir for 1 hour, then stopped the reaction and carried out post-treatment using the following method: The reaction solution was extracted three times and the organic layers were combined, and the organic layer was washed twice with water and saturated brine. Then add anhydrous sodium sulfate for drying, and finally perform column chromatography through a silica gel column (DCM:MeOH=...

Embodiment 2

[0047] Embodiment 2: the preparation of A2

[0048] Except that 2-nitrobenzyl bromide is used to replace 2-naphthylmethyl bromide in Example 1, and the reaction temperature is 50° C., other conditions and steps are the same as in Example 1 to obtain Compound A2 (56% yield, 97% deuteration rate). %).

[0049] Pale yellow solid. 1 H NMR (300MHz, CDCl 3 ):δ10.41(s,0.03H),8.10-8.13(m,1H),7.94-7.97(m,1H),7.30-7.83(m,2H). 13 C NMR (75MHz, CDCl 3 ):δ187.8(t,J C-D =29.2Hz), 149.6, 134.1, 133.7, 131.3, 129.7, 124.5.

Embodiment 3

[0050] Embodiment 3: the preparation of A3

[0051] Except that 4-cyanobenzyl bromide was used instead of 2-naphthylmethyl bromide in Example 1, other conditions and steps were the same as in Example 1 to obtain compound A3 (yield 84%, deuteration rate 97%).

[0052] white solid. 1 H NMR (600MHz, CDCl 3 ):δ10.09(s,0.03H),7.98(d,2H,J=8.4Hz),7.83(d,2H,J=8.4Hz). 13 C NMR (150MHz, CDCl 3 ):δ189.8(t,J C-D =27.0Hz), 138.2, 132.4, 129.4, 117.2, 117.1.

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Abstract

The invention provides a method for preparing deuterated aldehydes by using halomethyl compounds as raw materials. Described method comprises the steps: in the solvent that pyridine compound exists and D 2 Add halomethyl compounds to O mixed liquid, and react at 0°C~100°C; then add nitrosobenzene compounds to continue the reaction, and finally the reaction liquid is acidified to obtain the target product. The raw materials used in the method of the present invention are all cheap and easy to obtain, no expensive reagents or heavy metal raw materials are required, and the reaction conditions are simple, without harsh conditions such as high temperature, that is, the preparation method of the present invention is low in cost, simple in operation, and high in deuterium substitution rate. Up to 97%, the target product is easy to purify and the yield is high, up to 95%. Moreover, the substrate of the method of the present invention has wide applicability, and various deuterated aldehyde compounds can be prepared.

Description

technical field [0001] The invention belongs to the field of compound preparation, and more specifically relates to a method for preparing deuterated aldehydes by using halomethyl compounds as raw materials. Background technique [0002] Aldehydes play an irreplaceable role in many chemical transformations. Deuterated aldehydes and their derivatives have various practical applications, such as metabolic pathway probes and reaction mechanism studies. Although the synthesis of aldehydes has been extensively studied, the efficient synthesis of 1-deuterated aldehydes is still very challenging, and therefore, efforts have been made to expand the methods for the synthesis of deuterated aldehydes. [0003] The traditional preparation method of deuterated aldehyde mainly includes the deuterated reduction of the corresponding ester, followed by oxidation, using D 2 The gas undergoes Rosenmund reduction of acid chlorides, H / D exchange of dithiol-protected aldehydes, reduction of dih...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/00C07C47/542C07C47/546C07C47/548C07C47/55C07C47/575C07C47/232C07C65/42C07C201/12C07C205/44C07C253/30C07C255/56C07D213/48C07D215/54C07D277/32C07D333/56C07D263/32C07B59/00
CPCC07B59/001C07B59/002C07B2200/05C07C45/00C07C201/12C07C253/30C07D213/48C07D215/54C07D263/32C07D277/32C07D333/56C07C47/542C07C47/546C07C47/548C07C47/55C07C47/575C07C47/232C07C65/42C07C205/44C07C255/56
Inventor 罗海彬盛春泉李祥民武善超陈树强吴德燕
Owner SUN YAT SEN UNIV
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