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An optically active, derivative technology, applied in organic chemistry and other directions, can solve problems such as expensive, large number of catalysts
Active Publication Date: 2014-04-23
NIPPON SODA CO LTD
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[0017] On the other hand, when performing an asymmetric dialkylation reaction represented by the following formula (M-2), which is a reaction similar to the above-mentioned reaction using the same catalyst, although the optical yield is good, the use of base is extremely expensive cesium hydroxide, and requires a large amount of catalyst (S / C=100) (Patent Document 2)
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Embodiment 1
[0343] [Example 1] Optically active 6,7-dihydro-5H-dibenzo[c,e]azepine Synthesis of Derivatives
Embodiment 1-1
[0345]
[0346] Synthesis of Step 1(S)-1
[0347] Chiral diphenol (0.5 mmol) and potassium carbonate base (1.5-2 mmol) were dissolved in acetonitrile (50 mL) solvent. While refluxing, 1,4-dibromobutane was slowly added dropwise. After 3 hours, acetonitrile was distilled off under reduced pressure, followed by extraction and drying. After concentration under reduced pressure, it was simply purified with a short column of silica gel and used in the next step (yield 87%).
[0348] 1 H NMR (300MHz, CDCl 3 )δ7.51 (2H, d, J=8.7Hz, ArH), 6.84 (2H, d, J=8.7Hz, ArH), 4.30-4.38 (2H, m, ArOCH 2 ), 3.90-3.99 (2H, m, ArOCH 2 ), 2.07 (6H, s, ArCH 3 ), 1.61-1.79 (4H, m, CH 2 );[α] D 29 +118.2° (c 1.0, CHCl 3 ).
[0349] Synthesis of Step 2(S)-2
[0350] Under argon atmosphere, in the presence of palladium acetate (5mol%) p-tolyltriphenylphosphine (20mol%) catalyst, using potassium phosphate (5e.q.) as a base, in DMF (5mL) solvent, make aromatic Suzuki coupling of aryl bromide...
Embodiment 1-2
[0359] The compound of Example 1-2 was synthesized in the same manner as in Example 1-1.
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Abstract
It is to provide a novel optically active dibenzazepine derivative having a high utility value as an asymmetric phase-transfer catalyst. It is an optically active 6,7-dihydro-5H-dibenzo[c,e]azepine derivative represented by the following formula (1'), (wherein R represents a divalent organic group for cross-linking the 1 st position and the 11 th position; R 1 and R 2 are the same or different, and represent a hydrogen atom, halogen atom, or organic group, or R 1 and R 2 together represent a divalent organic group; R 3' and R 4' are the same or different and represent a monovalent organic group, or R 3' and R 4' together form an organic group that forms a cyclic structure comprising an onium nitrogen atom; Ar represents a monovalent organic group; * represents optical activity, i.e., that one axially asymmetric isomer is present in excess of the other axially asymmetric isomer with respect to a bond axis that constitutes the biphenyl structure of the compound; and X - represents a counter anion).
Description
technical field [0001] The present invention relates to optically active dibenzoazepines Derivatives, in detail, relate to novel compounds with high utility value as asymmetric phase transfer catalysts in fields related to the production of optically active raw materials, intermediates, starting materials, etc., centering on pharmaceuticals and agricultural chemicals. optically active quaternary ammonium salts. Background technique [0002] There are proposals for various optically active quaternary ammonium salts that are useful as asymmetric phase transfer catalysts, especially optically active 6,7-dihydro-5H-dibenzo[c,e]azepine Backbone compounds are useful. Such compounds include compounds represented by the following formula (L-1a) described in Patent Document 1, [0003] [0004] (In the formula, * represents optical activity, that is, one axially asymmetric isomer is more than the other axially asymmetric isomer with respect to the bond axis constituting the b...
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