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Chiral salen catalyst and methods for prepn. of chirol compounds from racemic epoxides by using new catalyst

A technology for chiral compounds and catalysts, applied in chemical instruments and methods, organic chemistry methods, cobalt organic compounds, etc., can solve problems such as restrictions on reuse and increase the manufacturing price of chiral epoxides

Inactive Publication Date: 2003-12-24
RSTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, reuse is limited
These issues drive up the manufacturing price of chiral epoxide production

Method used

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  • Chiral salen catalyst and methods for prepn. of chirol compounds from racemic epoxides by using new catalyst
  • Chiral salen catalyst and methods for prepn. of chirol compounds from racemic epoxides by using new catalyst
  • Chiral salen catalyst and methods for prepn. of chirol compounds from racemic epoxides by using new catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Hereinafter, the present invention will be described in more detail using examples. However, this should not be construed as limiting the scope of the invention. Embodiment 1: the preparation of I-SS-1

[0063] Mix 1 equivalent of (S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine and 1.2 equivalents of cobalt acetate in ethanol (II) 4H 2 O, and reflux for 5 hours with stirring. The reaction mixture was filtered and washed with a small amount of ethanol. The obtained solid was mixed with 0.5 equivalent of boron trifluoride·2H 2 O was mixed in dichloromethane and the reaction mixture was stirred at room temperature for 4 hours. Dichloromethane was removed under reduced pressure to yield the desired compound.

[0064] IR 70, 1010, 1070, 1100, 1220, 1270, 1360, 1560, 1720cm -1 ;

[0065] UV / visible light 360nm;

[0066] 13 C NMR (CDCl 3 , ppm) δ17.62, 22.33, 24.42, 29.57, 31.51, 32.34, 33.70, 42.93, 47.03, 56.53, 82.37, 92.93, 97.47, 126.18; ...

Embodiment 2

[0069] Analysis calculation (C 72 h 104 N 4 o 4 co 2 ·BF 3 ·3H 2 O) C 65.1, H 8.3, N 4.2, found C 65.4, H 8.5, N 4.2. Embodiment 2: Preparation of I-RR-1 a) Except that (S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is replaced by

[0070] (R, R)-N, N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, using the above

[0071] The same method in Example 1 was used to obtain the target product.

[0072] IR 970, 1010, 1070, 1100, 1220, 1270, 1360, 1560, 1720cm -1 ;

[0073] UV / visible light 360nm;

[0074] 13 C NMR (CDCl 3 , ppm) δ 17.62, 22.33, 24.42, 29.57, 31.51, 32.34, 33.70, 42.93, 47.03, 56.53, 82.37, 92.93, 97.47, 126.18;

[0075] 19 F NMR (CDCl 3 )(CFCl 3 , ppm) δ-87.62;

[0076] 11 B NMR (CDCl 3 )(BF 3 , ppm) δ0.31; and

[0077] Analysis calculation (C 72 h 104 N 4 o 4 co 2 ·BF 3 ·3H 2 O) C 65.1, H 8.3, N 4.2, found C 65.4, H 8.5, N 4.2. b) Except that (S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohex...

Embodiment 3

[0083] The target product was obtained in the same manner as in Example 1 above. Embodiment 3: the preparation of I-SS-2

[0084] Except replacing (S,S)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine with (S)-N-(3, 5-di-tert-butyl salicylidene)-(S)-N'(salicylidene)-1,2-cyclohexanediamine, using the same method as in Example 1 above to obtain the desired product .

[0085] IR 970, 1010, 1070, 1100, 1220, 1270, 1360, 1560, 1720cm -1 ;and

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Abstract

There are provided new chiral salen catalyst, and methods for the preparation of chiral compounds from racemic epoxides by using new catalyst. More particularly, there are provided new chiral compounds from racemic epoxides by using new catalyst. More particularly, there are provided new chiral salen catalyst which has new molecular structure, which can be recycled without any additional regeneration process because the catalyst retains its catalystic activity even after the repeated use, and which causes no or little racemization which results from the reverse reaction of the produced chiral compound, and methods for the mass production of chiral compounds, which is useful as an intermediate for the manufacture of drugs and food additives, from racemic epoxides by using the catalyst in an economic manner and with high optical purity.

Description

technical field [0001] The present invention relates to novel chiral salen catalysts and a process for the preparation of chiral compounds from racemic epoxides by using the novel catalysts. More specifically, the present invention provides novel chiral salen catalysts and their use for the production of chiral compounds with high optical purity, which are used as large-scale, economical preparations of chiral drugs or food additives Raw materials in which the chiral salen catalyst with a specific molecular structure can be continuously reused without any activation process of the used catalyst, and since it maintains its catalytic activity after the reaction process, does not cause or only causes Very little racemization. Background technique [0002] Chiral epoxides or chiral 1,2-diols have been widely used to prepare pharmaceuticals, agricultural products and food additives with optical properties (USP 5,071,868; Tetrahedron Lett., Vol.28, No.16, 1783, 1987; J. Org. Che...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/32B01J23/75B01J31/18B01J31/22B01J31/26C07B53/00C07B61/00C07C29/10C07C31/20C07D303/04C07D303/12C07D303/22C07D303/40
CPCB01J2531/847B01J2531/62B01J2531/845B01J2531/72B01J2531/0252B01J23/75B01J31/403B01J2531/842B01J2531/64B01J31/26B01J31/2243B01J2231/487
Inventor 金建中李浩诚金镐喆尹鉁远金成镇
Owner RSTECH CO LTD