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Optically active dibenzazepine derivatives

An optically active and derivative technology, applied in organic chemistry and other fields, can solve problems such as expensive and large quantities of catalysts

Active Publication Date: 2011-03-02
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[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)

Method used

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  • Optically active dibenzazepine derivatives
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Examples

Experimental program
Comparison scheme
Effect test

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.

[0360]

[0361] 1 H NMR (300MHz, CDCl 3 )δ7.62-8.30 (6H, br, ArH), 7.47 (2H, d, J=8.7Hz, ArH), 7.39 (2H, d, J=8.7Hz, ArH), 4.45-4.66 (2H, m, ArOCH 2 ), 4.55 (2H, d, J=13.8Hz, ArCH 2 N), 4.33 (2H, t, J=9.3Hz, ArOCH 2 ), 3.94 (2H, d, J=13.8Hz, ArCH 2 N), 3.20-3.38 (2H, m, NCH 2 ), 2.62-2.80 (2H, m, NCH 2 ), 1.82-2.15 (4H, m, CH 2 ), 0.55-1.65 (12H, m, CH 2 , CH 3 ), 0.16-0.35 (2H, m, CH 2 );[α] D 26 -72.9° (c 1.0, MeOH).

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Abstract

The invention provides novel optically active dibenzazepine derivatives having high utility value as chiral phase-transfer catalyst, more specifically, optically active 6,7-dihydro-5H-dibenz-[c,e]azepine derivatives represented by general formula (1') [wherein R is a divalent organic bridging group for joining the 1- and 11-positions; R1 and R2 may be the same or different and are each hydrogen, halogeno, or an organic group, or R1 and R2 may together represent an divalent organic group; R3' and R4' may be the same or different and are each a monovalent organic group, or R3' and R4' may together represent a cyclic organic group containing the onium nitrogen atom; Ar is a monovalent organic group; * represents optical activity, that is, an excess of one axially chiral isomer over the other axially chiral isomer, both isomers being due to the bond axis constituting the biphenyl structure of the derivative; and X- is 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/16C07D317/60
CPCC07D491/20C07D491/16C07D491/06C07D317/60
Inventor 久保田靖井上勉
Owner NIPPON SODA CO LTD
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