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Adamantane derivatives and process for producing them

a technology of adamantane and derivatives, which is applied in the direction of organic compounds/hydrides/coordination complexes, organic chemistry, physical/chemical process catalysts, etc., can solve the problems of difficult introduction of hydroxyl groups (specifically, a plurality of hydroxyl groups) to adamantane by using these processes

Inactive Publication Date: 2007-07-24
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This process efficiently produces adamantane derivatives with desired functional groups, enhancing their optical and pharmaceutical applications by improving transformation rates and selectivity, thus overcoming the limitations of previous methods.

Problems solved by technology

Such excellent characteristics cannot be achieved by using conventional polymers.
However, introduction of a hydroxyl group (specifically, a plurality of hydroxyl groups) to adamantane by using these processes is difficult.

Method used

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  • Adamantane derivatives and process for producing them
  • Adamantane derivatives and process for producing them
  • Adamantane derivatives and process for producing them

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0227]Mixture of 10 mmole 1-acetylaminoadamantane (Aldrich chemical Company, Inc.), 1 mmole of N-hydroxyphthalimide (NHPI), 0.05 mmole of vanadium (III) acetylacetonato (V(AA)3) and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 1 (temperature and time). The products in the reaction mixture were analyzed by gas chromatography, and, as a result, 1-acetylamino-3-adamantanol (compound 1), 1-acetylamino-3,5-adamantanediol (compound 2) and 1-acetylamino-4-adamantanone (compound 3) were obtained with conversions and yields represented in Table 1.

[0228]

TABLE 1TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.3756896416860209266194Comp.1 (compound 1): 1-acetylamino-3-adamantanol Comp.2 (compound 2): 1-acetylamino-3,5-adamantanediol Comp.3 (compound 3): 1-acetylamino-4-adamantanone

example 2

[0229]A reactor was charged with 10 mmole of adamantane, 1 mmole of NHPI, 0.005 mmole of Co(AA)2 and 25 mL of acetic acid, then equipped with a gas bag of mixed gas (a mixed gas of 2 L of carbon monoxide and 0.5 L of oxygen). The resultant mixture was stirred for 6 hours at a temperature of 60° C. to give 1-carboxyadamantane and 1,3-dicarboxyadamantane.

[0230]A mixture of 10 mmole of 1-carboxyadamantane, 1 mmole of NHPI, 0.05 mmole of V(AA)3 and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 2 (time and temperature). As a result, 1-carboxy-3-adamantanol (compound 1), 1-carboxy-3,5-adamantanediol (compound 2) and 1-carboxy-4-adamantanone (compound 3) were obtained with conversions and yields represented in Table 2.

[0231]

TABLE 2TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.3751644483752785912475590641947589452295Comp.1 (compound 1): 1-carboxy-3-adamantanol Comp.2 (compound 2): 1-carboxy-3,5-adamantanediol Comp.3 (co...

example 3

[0232]In the presence of an acid catalyst (p-toluenesulfonic acid), 1-carboxyadamantane obtained in Example 2 was allowed to react with an excess amount of ethanol to give 1-ethoxycarbonyladamantane.

[0233]A mixture of 10 mmole of the 1-ethoxycarboxyadamantane, 1 mmole of NHPI, 0.05 mmole of V(AA)3 and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 3 (temperature and time). As a result, 1-ethoxycarbonyl-3-adamantanol (compound 1), 1-ethoxycarbonyl-3,5-adamatanediol (compound 2) and 1-ethoxy-4-carbonyladamantanone (compound 3) were obtained with conversions and yields represented in Table 3.

[0234]

TABLE 3TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.375695581687538668676066348646020925416775159927435Comp.1 (compound 1): 1-ethoxycarbonyl-3-adamantanol Comp.2 (compound 2): 1-ethoxycarbonyl-3,5-adamantanediol Comp.3 (compound 3): 1-ethoxycarbonyl-4-adamantanone

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Abstract

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3;or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.

Description

[0001]This application is the national phase under 35 U.S.C. §371 or prior PCT International Application No. PCT / JP98 / 00904 which has an International filing date of Mar. 5, 1998 which designated the United States of America, the entire contents of which are hereby incorporated by reference.TECHNICAL FIELD[0002]This invention relates to a novel adamantane derivative, which has a hydroxyl group together with a nitro group, an amino group, an acyloxy group, a carboxyl group, a hydroxymethyl group or the like, and to a process for producing the same.BACKGROUND ART[0003]The adamantane has a three-dimensionally symmetric structure and skeletons which insure mutual stabilization of each ring, and, as a result, endowed with distinctive functions. Various copolymers each having enhanced or improved functions or characteristics can be obtained by introducing a hydroxyl group into an adamantane and, if necessary, inducing them into an acrylic acid derivative or a carbonate. There have been pr...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C35/22C07C211/00C07C61/12C07D207/40C07D207/444B01J31/00C07C69/757C07C29/50C07C35/37C07C62/06C07C62/24C07C69/00C07C69/96C07C205/18C07C205/41C07C205/55C07C219/24C07C233/23C07C233/32C07C233/74C07C235/40C07C265/10C07C271/34
CPCC07C29/50C07C35/37C07C62/06C07C62/24C07C67/05C07C67/08C07C67/29C07C67/31C07C68/02C07C69/757C07C69/96C07C205/18C07C205/41C07C205/55C07C219/24C07C233/23C07C233/32C07C233/74C07C235/40C07C265/10C07C271/34C07C2603/74C07C69/753C07C69/157
Inventor ISHII, YASUTAKANAKANO, TATSUYAHIRAI, NARUHISA
Owner DAICEL CHEM IND LTD
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