JPH09268179A - Production of optically active pyrimidylalkyl alcohol by spontaneous asymmetric synthesis - Google Patents

Abstract

PROBLEM TO BE SOLVED: To easily produce an optically active pyrimidylalkyl alcohol at a low cost, not requiring a physical or chemical asymmetric source by a spontaneous asymmetric synthesis. SOLUTION: A compound of formula I (R<1> is H or a 1-22C alkyl or alkenyl) is reacted with an alkyl metal of the formula R<2> n Zn [R<2> is a 1-22C alkyl or alkenyl; (n) is 2] in a solvent (e.g. toluene) at -30 to 50 deg.C to provide an optically active pyrimidylalkyl alcohol of formula II [(*) represents an asymmetric carbon] having excess of either an S-isomer or an R-isomer or an optical activity. Moreover, the purified optically active compound is obtained by repeating the same reaction by using the pyrimidylalkyl alcohol of formula II as a catalyst. The optically active compound capable of producing the optically active compound by using the optically active compound and not requiring a symmetric source such as an expensive optically active compound and a circularly polarized light at all.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing an optically active pyrimidylalkyl alcohol, and more particularly to an optically active pyrimidyl alkyl alcohol by a spontaneous asymmetric synthesis that requires no chemical or physical asymmetric source. The present invention relates to a method for producing dialkyl alcohol.

[0002]

2. Description of the Related Art Conventionally, optically active organic compounds have been used as pesticides, medicines, etc., including active vitamins, and also as catalysts for synthesizing them. As a method for producing these optically active compounds, an enantioselective asymmetric synthesis method in which an optically active substance as an asymmetric source is used as an asymmetric catalyst or an asymmetric ligand, or an optically active substance is bound to a reaction substrate A diastereoselective asymmetric synthesis method of reacting by a reaction is widely known. In addition, an absolute asymmetric synthesis method (HBKa) using a physical asymmetric source such as circularly polarized light
gen et al., Tetrahedron Letters, 27, 2479 pages, 1971.
Year) is known. Further, there is a method of obtaining an optically active compound by a method including a crystallization process, and for example, when sodium chlorate is crystallized from a solution of sodium chlorate which is an inorganic compound, a crystal that precipitates is spontaneously left by accident. Having either a left-handed or right-handed structure (Kond
epudi et al., Science, 250, 975 pages, 1990).

[0003]

The enantioselective asymmetric synthesis method is useful because it can synthesize a large amount of an optically active compound from a small amount of an asymmetric source, as compared with other means for synthesizing an optically active compound. However, an optically active compound is required as a catalyst or a ligand in the asymmetric reaction, and this optically active compound is very expensive due to the difficulty of preparation. In the diastereoselective asymmetric synthesis method, an optically active compound is required as a compound to be bonded to a reaction substrate, and an optically active compound which is expensive as in the enantioselective asymmetric synthesis is required as an asymmetric source. Further, in absolute asymmetric synthesis, since a physical asymmetric source such as circularly polarized light is required, an expensive device or the like is required, and the energy used for manufacturing is also very expensive. Further, the method using crystallization has an advantage that an asymmetric source is not required as compared with the above method, but the number of molecules is not increased by the reaction.

That is, in the conventional method for synthesizing an optically active compound, a chemical or physical asymmetric source is always required, and until now, an asymmetric synthesis which does not require an asymmetric source in the synthesis of an optically active compound. There is no law. Therefore, under the present circumstances, it is inevitable that the production cost of the optically active compound is increased.

In view of the above circumstances, the present invention does not require any physical or chemical asymmetric source (optically active substance, circularly polarized light, etc.) and can synthesize an optically active compound easily and at low cost. The basic purpose is to develop a method for producing an optically active compound.

[0006]

Means for Solving the Problems As a result of intensive studies conducted by the present inventors in accordance with the above-mentioned object, the inventors have reacted an alkyl metal with a pyrimidine ring derivative to give an excessive S- or R-isomer in absolute configuration, or an optical configuration. The present invention has been completed by developing a method for producing an active compound. That is, according to the present invention, the general formula (3)

[0007]

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The compound represented by the general formula (2)

[0009]

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An alkyl metal represented by the formula:

[0011]

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There is provided a process for producing a pyrimidyl alkyl alcohol, which comprises producing a compound represented by In the compound, when the S-configuration or R-configuration in the absolute configuration is in excess of a certain value or more, it has optical activity.

According to the present invention, a chemical or physical asymmetric source is not required at all, and in the absolute configuration, the ratio of the S isomer is higher than that of the R isomer, or the ratio of the R isomer is higher than that of the S isomer, or optical. Active pyrimidyl alkyl alcohols can be produced. The S-form or R-form excess or the optically active pyrimidylalkyl alcohol produced by the present invention serves as an asymmetric source. Or if the optical purity is lower than the desired ratio, the excess ratio can be increased by using other conventional means, and it can be used for other asymmetric synthesis and the like.

The excess or optically active pyrimidylalkyl alcohol of the S-form or R-form produced by the present invention is preferably increased in its excess ratio or optical purity by the following method. That is, using the pyrimidylalkyl alcohol having an excess of S-form or R-form or an optically active compound obtained by the above-mentioned production method as a catalyst, the compound of the general formula (3)

[0015]

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The compound represented by the general formula (2)

[0017]

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By adding an alkyl metal represented by the formula (1), the excess of S-form or R-form in absolute configuration is increased more than that of pyrimidylalkyl alcohol as a catalyst, or general formula (1) having high optical purity.

[0019]

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A synthetic reaction for producing a pyrimidylalkyl alcohol represented by the following is carried out, and the synthetic reaction is carried out using the produced pyrimidylalkyl alcohol as a catalyst.
By repeating this once or more, an optically active pyrimidyl alkyl alcohol having an optical purity of 2% or more can be obtained.

According to the above-mentioned production method, a pyrimidylalkyl alcohol having a high optical purity can be produced without any need for an optically active compound or a chemical or physical asymmetric source such as circularly polarized light. That is, since an expensive asymmetric source which has always been necessary for producing an optically active compound in the past is not used at all, the optically active compound can be produced easily and at low cost.

Also, the optical purity 2 produced by the present invention
A compound having an optical activity of more than 10% can be obtained by the following asymmetric autocatalytic reaction (K. Soai, T. Shibata, H. Morioka, K. Choj.
i, Nature, 378, p. 767, 1995) can further improve the optical purity of the optically active compound. That is, when used in combination with the production method according to the present invention, an optically active compound can be obtained with extremely high purity (90% or more) very easily and without any need for an asymmetric source.

[0023]

BEST MODE FOR CARRYING OUT THE INVENTION In R ¹ or R ² of the general formula (1), the general formula (2) and the general formula (3) in the present invention, the alkyl group is a methyl group, an ethyl group, a propyl group, Butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group,
A linear or branched group such as a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, an uneicosyl group, and a doeicosyl group can be used. As the alkenyl group, ethenyl group (vinyl group), propenyl group (allyl group), butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group. A linear or branched group such as a tetradecenyl group, a pentadecenyl group, a hexadecenyl group, a heptadecenyl group, an octadecenyl group, a nonadecenyl group, an eicosenyl group, an uneicosenyl group, and a doeicosenyl group may be used. Further, in R ¹ or R ² , a derivative of an alkyl group or an alkenyl group can also be used.

Further, in the general formula (1), the general formula (2) and the general formula (3) in the present invention, R ¹ is
It is preferably a hydrogen atom, or a linear or branched alkyl group or alkenyl group (having 1 to 22 carbon atoms). More preferably, a hydrogen atom, or a linear or branched alkyl group or alkenyl group (having 1 to 10 carbon atoms).
And particularly preferably, a hydrogen atom, or a linear or branched alkyl group or alkenyl group (having 1 to 1 carbon atoms).
5), most preferably a hydrogen atom or a methyl group. R ² is preferably a linear or branched alkyl group or alkenyl group (having 1 to 22 carbon atoms), and more preferably a linear or branched alkyl group or alkenyl group (having 1 to 10 carbon atoms). Yes,
A linear or branched alkyl group or alkenyl group (having 1 to 5 carbon atoms) is particularly preferable, and an isopropyl group is most preferable.

In the reaction according to the present invention, as the reaction organic solvent, toluene, xylene, mesitylene, cumene,
Benzene, pentane, hexane, heptane, octane,
Hydrocarbon compounds such as petroleum ether, diethyl ether,
It is preferable to use ether compounds such as dialkyl ether, tetrahydrofuran, dimethoxyethane, diglyme and anisole. Especially preferred is toluene.
That is, it is preferable to use an aldehyde dissolved in toluene or an alkyl metal toluene. It is preferable to use zinc as the metal element. That is, it is preferable to dissolve dialkylzinc in toluene and use it as a dialkyltoluene solution. In order to ensure the reaction, it is preferable to mix the above compounds with stirring over time. The reaction temperature is
It can be performed in the range of -30 ° C to 50 ° C. In order to carry out the reaction more reliably, it is preferable to carry out the reaction at low temperature. Most preferably, it is 0 ° C.

In addition, a step of adding a solution containing an alkyl metal to a solution containing a compound represented by the general formula (3) and then reacting the solution by stirring for a predetermined time, that is, an alkyl metal It is preferable to produce the optically active pyrimidylalkyl alcohol by repeating the addition of the solution and the reaction at least once, and a solution containing the compound of the general formula (3) may be added to the reaction solution, if necessary. As a result, in one system, it becomes possible to produce a compound of high optical purity from a state without a chiral source,
It is possible to easily produce an optically active pyrimidylalkyl alcohol having high optical purity.

[0027]

Embodiments of the present invention will be described below in more detail. However, the invention is in no way limited to these examples. In addition, "ee" means "enantiomeric excess (%)".

The chemical formulas and reaction formulas of the compounds used in the following Examples 1 to 4 are shown in the following figures. In the figure below, 3a is pyrimidine-5-carboxaldehyde, 3b is 2-methylpyrimidine-5-carboxaldehyde, 1a is 2-methyl-1- (5-pyrimidyl) -1-propanol, 1a.
b is 2-methyl-1- (2-methyl-5-pyrimidyl)
-1-Represents propanol.

[0029]

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<Example 1> (1) Pyrimidine-5-carboxaldehyde (3a)
(1 mmol) was dissolved in toluene (44.8 ml). Diisopropyl zinc toluene solution (1.2
Milliliter, concentration 1M) at 0 ° C, then 0 ° C
The mixture was stirred for 72 hours. The reaction was stopped by adding hydrochloric acid (concentration 1M), and further, 15 ml of a saturated aqueous sodium hydrogen carbonate solution was added to make the liquid alkaline. The mixture was filtered using Celite, and the filtrate was extracted with ethyl acetate. The extract was dried with anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was separated and purified using a silica gel thin layer chromatograph to obtain 2-methyl-1- (5-pyrimidyl) -1-propanol (1a) in an amount of 0.54 mmol (yield 54%).

(2) 2-Methyl-1 synthesized in (1)
-(5-Pyrimidyl) -1-propanol (1a)
(0.2 mmol, 20 mol%) was dissolved in toluene (44.8 ml) as a catalyst. Diisopropyl zinc (1.2 mmol) toluene solution (1.2 ml, concentration 1M) was added at 0 ° C., and the mixture was stirred for 30 minutes. Pyrimidine-5-carboxaldehyde (3a)
1.8 ml of a toluene solution of (1 mmol) was added, and the mixture was stirred at 0 ° C. for 24 hours. When the reaction was stopped and post-treated in the same manner as in (1), 2-methyl-1
There was obtained 0.68 mmol of-(5-pyrimidyl) -1-propanol (1a) (yield 68%, including the alcohol initially used as the catalyst).

(3) 2-Methyl-1 synthesized in (2)
-(5-Pyrimidyl) -1-propanol (1a)
2-Methyl-1- (5-pyrimidyl) -1-propanol was prepared in the same manner as in (2) except that (0.2 mmol, 20 mol%) was used as a catalyst and the reaction time was 42 hours. 0.65 mmol of (1a) was obtained (yield 65%, including the alcohol initially used as the catalyst).

(4) 2-Methyl-1 synthesized in (3)
-(5-Pyrimidyl) -1-propanol (1a)
2-Methyl-1- (5-pyrimidyl) -1-propanol was prepared in the same manner as in (2) except that (0.2 mmol, 20 mol%) was used as a catalyst and the reaction time was 120 hours. 0.56 mmol of (1a) (yield 56%, including the alcohol initially used as the catalyst) was obtained.

(5) 2-Methyl-1 synthesized in (4)
-(5-Pyrimidyl) -1-propanol (1a)
2-Methyl-1- (5-pyrimidyl) -1-propanol was prepared in the same manner as in (2) except that (0.2 mmol, 20 mol%) was used as a catalyst and the reaction time was 42 hours. 0.65 mmol of (1a) was obtained (yield 65%, including the alcohol initially used as the catalyst). The optical purity of the obtained alcohol (1a) was determined by the analysis method using a polarimeter, and the specific optical rotation [α] _D ²³ (2 for the D line of sodium was measured).
The specific optical rotation at 3 ° C.) is + 1.46 °, and the optical purity is 2.6% by the analytical method by high performance liquid chromatography using a chiral column (Daicel Chiralcel OD). e. Met.

(6) Optically active 2-methyl-1- (5-
Pyrimidyl) -1-propanol (1a) is used to propagate asymmetry by an asymmetric autocatalytic reaction.
78, p. 767, 1995).
I followed this. That is, 2-methyl-synthesized in (5)
1- (5-pyrimidyl) -1-propanol (1a)
2-Methyl-1- (5-pyrimidyl) -1-propanol was prepared in the same manner as in (2) except that (0.2 mmol, 20 mol%) was used as a catalyst and the reaction time was 26 hours. 0.61 mmol of (1a) was obtained (61% yield, including the alcohol initially used as the catalyst). The optical purity of the obtained alcohol (1a) was determined by an analysis method using an optical polarimeter, with a specific optical rotation [α] _D ²³ of + 8.29 ° (c 1, methanol), and a high-speed liquid using a chiral column (Daicel Chiralcel OD). Chromatographic analysis provides optical purity of 14.8% e. e. Met. Also, the absolute placement is (R)
It was -1a. That is, a compound with high optical purity could be produced from the state without any asymmetric source.

Example 2 (1) The reaction was carried out under the same conditions as in Example 1 (1) (however, the reaction time was 24 hours) to give 2-methyl-1- (5-pyrimidyl) -1-. 0.45 mmol (yield 45%) of propanol (1a) was obtained.

(2) 2-Methyl-1-obtained in (1)
Except that (5-pyrimidyl) -1-propanol (1a) was used as a catalyst, the same operation as in (2) of Example 1 (reaction time was 24 hours) was performed to prepare 2-methyl-1- (5- Pyrimidyl) -1-propanol (1a) yield 58%
(Including alcohol used as catalyst).

(3) 2-Methyl-1-obtained in (2)
Except that (5-pyrimidyl) -1-propanol (1a) was used as a catalyst, the same operation as in (2) of Example 1 (reaction time was 24 hours) was performed to prepare 2-methyl-1- (5- Pyrimidyl) -1-propanol (1a) yield 52%
(Including alcohol used as catalyst).

(4) 2-Methyl-1-obtained in (3)
Except that (5-pyrimidyl) -1-propanol (1a) was used as a catalyst, the same operation as in (2) of Example 1 (reaction time was 24 hours) was performed to prepare 2-methyl-1- (5- Pyrimidyl) -1-propanol (1a) yield 57%
(Including alcohol used as catalyst).

(5) 2-Methyl-1-obtained in (4)
Except that (5-pyrimidyl) -1-propanol (1a) was used as a catalyst, the same operation as in (2) of Example 1 (reaction time was 24 hours) was performed to prepare 2-methyl-1- (5- Pyrimidyl) -1-propanol (1a) yield 58%
(Including alcohol used as catalyst). This alcohol is a chiral column (Daicel Chiralcel OD)
Optical purity of 3.2% e. e. Met. The absolute configuration is the (S) body, which is the reverse of that in Example 1, and the specific rotation [α] _D ²³ is -1.7 ° (c 1,
Methanol).

(6) 2-Methyl-1-obtained in (5)
Except that (5-pyrimidyl) -1-propanol (1a) was used as a catalyst, the same operation as in (6) of Example 1 (reaction time was 24 hours) was performed to prepare 2-methyl-1- (5- Pyrimidyl) -1-propanol (1a) was obtained in an amount of 0.52 mmol (yield 52%, including alcohol used as a catalyst). The obtained alcohol had a specific optical rotation [α] _D ²³ of −5.9 ° (c 1, methanol) by an analysis method using a polarimeter, and had a chiral column (Daicel Chiralcel).
OD) by high performance liquid chromatography analysis with an optical purity of 13.9% e. e. Met. The absolute configuration was (S).

<Example 3> (1) When 2-methylpyrimidine-5-carboxaldehyde (3b) was used as the aldehyde, the reaction was conducted in the same manner as in (1) of Example 1 to give 2-methyl- 1-
(2-Methyl-5-pyrimidyl) -1-propanol (1b) was obtained with a yield of 85%. When the product (1b) was analyzed by high performance liquid chromatography using a chiral column (Daicel Chiralcel OD), the optical purity was 2.
3% e. e. And the absolute configuration was (S) -1b.

(2) The alcohol (1) obtained in (1)
b) was used as a catalyst in the same manner as in (2) of Example 1 to give 2
-Methylpyrimidine-5-carboxaldehyde (3
The reaction between b) and diisopropylzinc (reaction time was 24 hours) was carried out (yield 60%, including the alcohol used as the catalyst). As the alcohol of the product, the optical purity is 14.5% by the analysis method by high performance liquid chromatography using a chiral column (Daicel Chiralcel OD).
e. e. 2-Methyl-1- (2-methyl-5-pyrimidyl) -1-propanol (1b) was obtained. The absolute configuration of this alcohol (1b) was (S) -1b.

<Example 4> (1) When 2-methylpyrimidine-5-carboxaldehyde (3b) was used as the aldehyde, the reaction was conducted in the same manner as in (1) of Example 1 to give 2-methyl- 1-
(2-Methyl-5-pyrimidyl) -1-propanol (1b) was obtained with a yield of 82%. When the product (1b) was analyzed by high performance liquid chromatography using a chiral column (Daicel Chiralcel OD), the optical purity was 2.
2% e. e. And the absolute configuration was (R) -1b.

(2) Alcohol (1 obtained in (1)
b) was used as a catalyst in the same manner as in (2) of Example 1 to give 2
-Methylpyrimidine-5-carboxaldehyde (3
The reaction between b) and diisopropylzinc (reaction time was 24 hours) was performed (yield 55%, including the alcohol used as the catalyst). As the alcohol of the product, the optical purity was 13.9% by the analysis method by high performance liquid chromatography using a chiral column (Daicel Chiralcel OD).
e. e. 2-Methyl-1- (2-methyl-5-pyrimidyl) -1-propanol (1b) was obtained. The absolute configuration of this alcohol (1b) is R, which is the opposite of that in Example 3.
Body.

<Example 5> 2-Methylpyrimidine-5-
24.5 mg (0.20 mmol) of carboxaldehyde (3b) was dissolved in toluene (1.6 ml). The solution was cooled to 0 ° C. and 0.04 ml (0.04 mmol) of diisopropyl zinc toluene solution (concentration 1.0 M) was added. After stirring at room temperature for 1 hour, 0.12 ml (0.12 mmol) of diisopropyl zinc toluene solution (concentration 1.0 M) was added at 0 ° C., and the mixture was stirred at 0 ° C. for 2 hours. Further, 0.24 ml (0.24 mmol) of diisopropyl zinc toluene solution (concentration 1.0 M) was added and stirred for 16 hours. Hydrochloric acid (concentration 1M) 3 ml was added, saturated aqueous sodium hydrogen carbonate solution (12 ml) was further added, and the mixture was extracted with ethyl acetate (15 ml 3 times). The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was separated and purified by silica gel thin layer chromatography (developing solvent: hexane / acetone = 1/1).
(S) -2-Methyl-1- (2-methyl-5-pyrimidyl) -1-propanol (1b) 24.6 mg (yield 74%), asymmetric yield 18.6% e. e. I got it.

Example 6 2-Methylpyrimidine-5-
12.2 mg (0.10 mmol) of carboxaldehyde (3b) was dissolved in toluene (1.0 ml). The solution was cooled to 0 ° C. and 0.025 ml (0.025 mmol) of diisopropyl zinc toluene solution (concentration 1.0 M) was added. After stirring at room temperature for 1 hour, 0.075 ml (0.075 ml) of diisopropyl zinc toluene solution (concentration 1.0 M) was added at 0 ° C.
Mmol) was added and the mixture was stirred at 0 ° C. for 2 hours. Furthermore, diisopropyl zinc toluene solution (concentration 1.0M) 0.1
Milliliter (0.1 mmol) was added and stirred for 8 hours. Next, at 0 ° C., 0.70 ml (0.70 mmol) of diisopropyl zinc toluene solution (concentration 1.0 M) and 1.4 ml of toluene were added,
After stirring at 0 ° C for 10 minutes, 2-methylpyrimidine-
A solution of 4-8.8 mg (0.40 mmol) of 5-carboxaldehyde (3b) in toluene (1.5 ml) was added, and the mixture was stirred at 0 ° C for 14 hours. further,
Diisopropyl zinc toluene solution (concentration 1.0
2.8 ml (2.80 mmol) of M) and 9.1 ml of toluene were added, and the mixture was stirred at 0 ° C. for 10 minutes, and then 195.4 mg of 2-methylpyrimidine-5-carboxaldehyde (3b) (1. 6 mmol) in toluene (2.5 ml) was added and 0
The mixture was stirred at 0 ° C for 12 hours. 5 ml of hydrochloric acid (concentration 1M) was added, and saturated aqueous sodium hydrogen carbonate solution (1
5 ml) was added and the mixture was extracted with ethyl acetate (30 ml, three times). The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel thin layer chromatography (developing solvent: hexane / acetone = 1 /
Separation and purification in (1), (S) -2-methyl-1- (2-
Methyl-5-pyrimidyl) -1-propanol (1b)
315.9 mg (yield 90.5%), asymmetric yield 76.5% e. e. I got it.

[0048]

INDUSTRIAL APPLICABILITY According to the present invention, an optically active compound, a chemical or physical asymmetric source such as circularly polarized light is not required at all,
An S- or R-form excess compound or an optically active compound in absolute configuration can be produced. That is, since an excessive compound of S-form or R-form or an expensive asymmetric source which is always required for producing an optically active compound in the past is not used at all, an optically active compound can be produced easily and at low cost. Becomes

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical indication C07M 7:00

Claims (4)

[Claims] 1. A general formula (3): The compound represented by the general formula (2): By reacting an alkyl metal represented by the formula (1) with an excessive S or R isomer in absolute configuration or having optical activity A method for synthesizing a pyrimidyl alkyl alcohol, which comprises producing a compound represented by: 2. A compound of the general formula (3): embedded image using a pyrimidyl alkyl alcohol as a catalyst. The compound represented by the general formula (2): By reacting an alkyl metal represented by the formula (1) with an excess of S-form or R-form in absolute configuration increased or higher optical purity than the catalyst pyrimidylalkyl alcohol. A method for asymmetrically synthesizing an optically active pyrimidylalkyl alcohol, wherein the synthetic reaction for synthesizing a pyrimidylalkyl alcohol represented by Using the pyrimidyl alkyl alcohol produced by the method as a catalyst, in the second and subsequent synthetic reactions, the pyrimidyl alkyl alcohol synthesized by the previous synthetic reaction is used as a catalyst, Method for asymmetric synthesis of optically active pyrimidyl alkyl alcohols. 3. A general formula (3): For a solution containing a compound represented by the general formula (2): The step of adding the solution containing the alkyl metal represented by the formula and the step of reacting the added solution are repeated at least once to obtain a compound represented by the general formula (1): A method for asymmetrically synthesizing an optically active pyrimidylalkyl alcohol, which comprises producing an optically active pyrimidylalkyl alcohol. 4. X is zinc and n is 2.
4. The method for synthesizing a pyrimidyl alkyl alcohol according to any one of 3 above.