A kind of method of synthesizing chiral alcohol

A chiral alcohol and chiral technology, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve the problems of limited substrate scope and low atom economy, and achieves high reaction economic benefits and yields. High efficiency and high stereoselectivity

Active Publication Date: 2022-03-18
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such methods require the addition of an additional hydrogen source, have a limited substrate range, and are not atom-economical

Method used

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  • A kind of method of synthesizing chiral alcohol
  • A kind of method of synthesizing chiral alcohol
  • A kind of method of synthesizing chiral alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Under argon, 1-phenyl ethanol was 366 mg (3 mmol), 122 mg (1 mmol) of methylbenyl alcohol, 12 mg (0.01 mmol), tert-butoxide 112 mg (1 mmol) ) The mixture of dichloromethane is 20: 1 is a column, and the column chromatography is separated, and the structural formula is as follows:

[0020]

[0021] The yield of the above white solid was 64%, and the EE value of the EE value of high performance liquid chromatography was 86%, and its spectral data was: 1 HNMR (CDCL 3 400MHz) δ (PPM): 7.28 (D, J = 2Hz, 2H), 7.26 (S, 2H), 7.11 (S, 4H), 4.68 (DD, J = 7.6, 5.6Hz, 1H), 2.76-2.61 (m, 2H), 2.34 (S, 3H) 2.22-1.98 (m, 2H), 1.66 (BRS, 1H); 13 C NMR (CDCL 3 100 MHz) δ (PPM): 141.78, 138.87, 137.43, 135.39, 129.32, 129.20, 128.46, 126.06, 73.80, 40.60, 31.78, 21.25, 21.13; HRMS (ESI) M / Z: C 16 Hide 18 O [m + na] + Theoretical value 249.1249, measured value 249.1243.

Embodiment 2

[0023] In the present embodiment, 1-phenyl ethanol in Example 1 was replaced with equimola 1- (2-methylphenyl) ethanol, and the other steps were the same as in Example 1, to obtain a white solid of a structural formula:

[0024]

[0025] The yield of the white solid is 52%, and the high performance liquid chromatography has an EE value of 93%, and the spectrum data is: 1 H NMR (CDCL 3 400MHz) δ (PPM): 7.53 (D, J = 8.0 Hz, 1H), 7.30-7.18 (m, 3H), 7.15 (S, 4H), 4.97 (DD, J = 8.2, 4.6 Hz, 1h), 2.89-2.82 (m, 1H), 2.78-2.70 (m, 1H), 2.37 (S, 3H), 2.79 (S, 3H), 2.79 (M, 2H), 1.79 (BRS, 1H); 13 C NMR (CDCL 3 100 MHz) δ (PPM): 142.9, 138.8, 135.3, 134.5, 130.4, 129.1, 128.4, 127.2, 126.3, 125.2, 69.9, 39.6, 31.8, 21.1, 19.0; HRMS (ESI) M / Z: C 17 Hide 20 O [m + na] + Theoretical value 263.1406, the measured value 263.1404.

Embodiment 3

[0027] In the present embodiment, 1-phenyl ethanol in Example 1 was replaced in an equimola 1- (2,4-dimethylphenyl) ethanol, and the reaction was reacted for 8 hours, and the other steps were the same as in Example 1. White solids as follows:

[0028]

[0029] The yield of the white solid is 75%, and the EE value of the EE is 92%, and the spectrum data is: 1 H NMR (CDCL 3 400MHz) δ (PPM): 7.39 (D, J = 7.6Hz, 1H), 7.12 (S, 4H), 7.06 (D, J = 8.0 Hz, 1H), 6.98 (S, 1H), 4.91 (DD, J = 8.0, 4.6Hz, 1H), 2.85-2.74 (m, 1H), 2.72-2.66 (m, 1H), 2.35 (S, 3H), 2.25 (S, 3H), 2.09 (S, 3H), 2.09 -1.99 (m, 2H), 1.79 (BRS, 1H); 13 C NMR (CDCL 3 100 MHz) δ (PPM): 139.9, 138.9, 136.9, 135.4, 134.6, 131.3, 129.2, 128.4, 127.1, 125.3, 70.1, 39.6, 32.0, 21.1, 39.0; HRMS (ESI) m / z: c 18 Hide 22 O [m + na] + Theoretical value 277.1562, measured value 277.1561.

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Abstract

The invention discloses a method for synthesizing chiral alcohols. The method uses a chiral ruthenium complex coordinated by diphosphine and dinitrogen as a catalyst, and uses racemic 1-arylethanol compounds and benzyl alcohol compounds as bases. Compounds, potassium tert-butoxide, etc. are used as bases to realize the synthesis of chiral alcohols through asymmetric hydrogen borrowing reactions in an inert gas atmosphere. The reaction system of the present invention is simple, easy to operate, does not require an additional hydrogen source, and the post-reaction treatment is simple. The yield of chiral alcohol is good and the stereoselectivity is high. Among them, the chiral alcohol of S configuration is the main one, and the range of substrates is It is a clean, safe and efficient method for synthesizing chiral alcohols with a wide range and high atom utilization.

Description

Technical field [0001] The present invention belongs to the technical field of synthetic chiral alcohols, and more particularly to 1-aryl ethanol and benzyl alcohol compounds to synthesize chiral alcohols by asymmetric leeilization process under chiral rhodium catalysis. Background technique [0002] Chiral alcohol is an important alcohol compound that is widely present in drugs, pesticides, food, synthetic intermediates, natural products, and biologically active compounds, especially in the field of chiral pharmaceuticals. The enantiomers of chiral drugs have very similar physical properties, however they have different pathways in biological metabolism, transformation or activation, resulting in a large phase of pharmacokine, so obtaining high-align selectivity or high non-related selection Single isomers have important significance. [0003] Conventional chemical synthesis methods are mainly asymmetric to be asymmetrically reduced by adding a chiral catalyst. Such methods are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/24C07C29/34C07C43/23C07C41/30C07C33/46C07C33/18C07C323/19C07C319/20C07D295/096C07D307/42C07D333/16C07D213/30C07D317/54
Inventor 王超王昆许瑞瑞汤卫军薛东李超群肖建良
Owner SHAANXI NORMAL UNIV
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