Preparation method of deuterated alcohol or deuterated amine compounds

A compound and alcohol technology, applied in the preparation of organic compounds, amino compounds, hydroxyl compounds, etc., can solve the problems of dangerous reaction process, harsh reaction conditions, poor selectivity, etc., to reduce the risk, mild reaction conditions, A stable effect

Active Publication Date: 2019-08-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through the selection of deuterium source, the study of reaction conditions and the improvement of reagents used in the reaction, the defects of the prior art such as expensive deuterium source, dangerous reaction process, harsh reaction conditions, low deuterium substitution rate and poor selectivity can be improved.

Method used

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  • Preparation method of deuterated alcohol or deuterated amine compounds
  • Preparation method of deuterated alcohol or deuterated amine compounds
  • Preparation method of deuterated alcohol or deuterated amine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Prepare benzhydryl alcohol (2a), structural formula is as follows:

[0101]

[0102] The reaction equation is as follows:

[0103]

[0104] According to the typical experimental procedure, with benzophenone (1a) (0.0364g, 0.2mmol), catalyst Ir-9 (0.9mg, 0.5mol%), N,N-dicyclohexylmethylamine (86μL, 0.4mmol), Li 2 CO 3 (8.9mg, 0.12mmol), heavy water (36μL, 2mmol), dissolved in 3mL ultra-dry acetonitrile for reaction. After the reaction, the crude product was purified by column chromatography (eluted with PE / EA=100 / 1~50 / 1) to obtain the target product (27mg, yield: 70%, 93% deuteration rate), the product It is a white solid. 1 HNMR (400MHz, CDCl 3 ):δ7.40–7.29 (m,8H), 7.29–7.25(m,2H), 2.33(s,1H). 13 CNMR (101MHz, CDCl 3 ): δ132.91– 116.81(m), 82.61–63.41(m).

Embodiment 2

[0106] Prepare 4-methyl-benzhydryl alcohol (2b), the structural formula is as follows:

[0107]

[0108] The reaction equation is as follows:

[0109]

[0110]According to the typical experimental procedure, with 4-methyl-benzophenone (1b) (0.0398g, 0.2mmol), catalyst Ir-7 (0.9mg, 0.5mol%), N,N-dicyclohexylmethylamine (86μL , 0.4mmol), Li 2 CO 3 (8.9mg, 0.12mmol), D 2 O (36 μL, 2 mmol), dissolved in 3 mL ultra-dry acetonitrile for reaction. After the reaction, the crude product was purified by column chromatography (eluted with PE / EA=100 / 1~50 / 1) to obtain the target product (27.9 mg, yield: 70%, 87% deuteration rate), the The product is a white solid. 1 H NMR (400MHz, CDCl 3 ):δ7.56–6.75(m,9H),2.32(s,3H),2.22(s,1H). 13 C NMR (101MHz, CDCl 3 ): δ143.98, 140.99, 137.40, 129.30, 128.57, 127.57, 126.61, 126.54, 76.19, 75.98, 75.76, 75.54, 21.24.

Embodiment 3

[0112] Prepare 2-chloro-benzhydryl alcohol (2c), the structural formula is as follows:

[0113]

[0114] The reaction equation is as follows:

[0115]

[0116] According to the typical experimental procedure, with 2-chloro-benzophenone (1c) (0.0433g, 0.2mmol), catalyst Ir-5 (0.9mg, 0.5mol%), N,N-dicyclohexylmethylamine (86μL, 0.4mmol), Li 2 CO 3 (8.9mg, 0.12mmol), D 2 O (36 μL, 2 mmol), dissolved in 3 mL ultra-dry acetonitrile for reaction. After the reaction, the crude product was purified by column chromatography (eluted with PE / EA=100 / 1~50 / 1) to obtain the target product (40.7 mg, yield: 94%, 89% deuteration rate), the The product is a white solid. 1 H NMR (400MHz, CDCl 3 ):δ7.86–6.77(m,9H),2.41(s,1H). 13 C NMR (101MHz, CDCl 3 ): δ142.24, 141.05, 141.00, 132.58, 129.65, 128.89, 128.60, 128.11, 127.91, 127.24, 127.04, 127.02, 72.78, 72.63, 72.40, 72.18.

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Abstract

Aiming at the defects in the prior art, the invention provides a simple method for producing and preparing deuterated alcohol or deuterated amine compounds. In the method, heavy water is used as a deuterium source, ketone or imine is used as a reaction raw material, and visible light or sunlight is used as an energy source; the reaction can be efficiently carried out at normal temperature and normal pressure. Through selection of a deuterium source, a catalyst and an electron donor, research on reaction conditions and improvement on reagents used in the reaction, the method can overcome the defects of expensive deuterium source, dangerous reaction process, rigorous reaction conditions, low deuteration rate, poor selectivity and the like in the prior art.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing deuterated alcohols and deuterated amines using heavy water as a deuterium source. Background technique [0002] Deuterated compounds are an important class of high value-added chemicals. In addition to being widely used as solvents in nuclear magnetic resonance spectroscopy, they also have important applications in exploring drug metabolism, revealing organic reaction mechanisms, and improving material properties. Especially in medicinal chemistry, the role of deuterium labeling has become increasingly prominent and has become an ideal drug modification method. Incorporation of deuterium into pharmacologically active drugs offers potential benefits such as improved exposure and reduced production of toxic metabolites, thereby enhancing efficacy, tolerability, or safety. Additionally, deuterated compounds have been extensively studied in non-clinical setti...

Claims

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Application Information

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IPC IPC(8): C07B59/00C07C29/143C07C33/24C07C33/46C07C41/18C07C43/23C07D213/38C07D333/20C07D307/52C07C209/00C07C211/27
CPCC07B59/001C07B59/002C07C29/143C07C41/18C07D213/38C07D333/20C07D307/52C07C209/00C07B2200/05C07C33/24C07C33/46C07C43/23C07C211/27
Inventor 樊新元代灿灿
Owner NANJING UNIV OF TECH
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