JPH0889261A - Production of optically active 1-(3,4-dimethoxyphenyl)-2-propanol - Google Patents

Abstract

PURPOSE: To obtain the subject compound useful e.g. as an intermediate for pharmaceuticals, physiologically active substances, etc., in high efficiency by treating 3,4-dimethoxyphenylacetone with a microorganism belonging to the genus Ambrosiozyma, etc., to effect the reduction of the compound and collecting the reaction product from the reaction liquid. CONSTITUTION: This optically active (S)-1-(3,4-dimethoxyphenyl)-2-propanol of formula II is produced by treating 3,4-dimethoxyphenylacetone of formula I with a microorganism belonging to the genus Ambrosiozyma, Candida, Cryptococcus, Clavispora, Debaryomyces, Di podascus, Filobasidium, Geotricum, Guilliermondella, Williopsis, Kluyveromyces, Lipomyces, Metschnikowia, Zygosaccharomyces, Alcaligenes, Arthrobacter, Bacillus, Micrococcus, Nocardis, Pseudomonas, Rhodococcus, etc., and collecting the produced reduction product from the reaction liquid.

Description

Detailed Description of the Invention

[0001]

The present invention relates to the formula (IV):

[0002]

[Chemical 5]

[0003] The present invention relates to a method for producing optically active 1- (3,4-dimethoxyphenyl) -2-propanol which is a useful intermediate for various pharmaceuticals and physiologically active substances.

[0004]

PRIOR ART AND PROBLEMS TO BE SOLVED BY THE INVENTION 1-
As a method for producing (3-methoxyphenyl) -2-propanol, Zu-Yun Cai et al. (Journal
Of Chemical Society Chemical Communication (J. Chem. Soc., Chem. Commun.), 1985,19,1277)
The method is known. This method uses 3-methoxyphenylacetone as a Saccharomyces cerevisiae.
yces cerevisiae) and asymmetric reduction of (S)
This gives-(3-methoxyphenyl) -2-propanol.

However, formula (I):

[0006]

[Chemical 6]

The 3,4-dimethoxyphenylacetone represented by the formula (1) is reduced with a microorganism to give the optically active 1- (3,4-dimethoxyphenyl) -formula represented by the formula (IV).
Nothing is known about the production of 2-propanol.

[0008]

DISCLOSURE OF THE INVENTION The present inventors have developed a simple and efficient optically active 1- (3,4) compound represented by the formula (IV).
As a result of diligent investigations on an industrial production method of -dimethoxyphenyl) -2-propanol, the compound represented by the formula (I)
The inventors have found a microorganism capable of stereoselectively reducing the carbonyl group of 4-dimethoxyphenylacetone to a hydroxyl group, and completed the present invention.

That is, the present invention has the formula (I):

[0010]

[Chemical 7]

In 3,4-dimethoxyphenylacetone represented by the following formula, genus Ambrosiothyma, genus Candida, genus Cryptococcus, genus Clavispora, genus Devariomyces, genus Dipoduscus, phyllobasidium, genus Geotricum, genus Guilliermondera, Williopsis,
Kluyveromyces genus, lipomyces genus, meschenicobia genus, pachysolene genus, pichia genus, rhodosporidium genus, kisstophyllobasidium genus, rhodotorula genus, saccharomyces genus, yarovia genus, saccharomycopsis genus, schwanniomyces Genus, Schizosaccharomyces, Sporideoboras, Sporoboromyces, Sterigmatomyces, Torulaspora, Trichosporon, Wickerahamia, Wingea, Digosaccharomyces, Alcaligenes, Arthrobacter, Bacillus, Micro From the step of reacting and reducing a microorganism selected from the group consisting of microorganisms belonging to the genera Coccus, Nocardia, Pseudomonas and Rhodococcus, and from the reaction solution, the formula (II):

[0012]

Embedded image

A step (S) -1- (3,4-dimethoxyphenyl) -2-propanol represented by the formula (II) comprising the step of collecting (S) -1-
It relates to a method for producing (3,4-dimethoxyphenyl) -2-propanol.

The present invention also has the formula (I):

[0015]

[Chemical 9]

A microorganism selected from the group consisting of microorganisms belonging to the genera Ashivia, Butrioascus, Candida, Rhodomomyces, Pichia, Rhodotorula, Trigonopsis and Pseudomonas in 3,4-dimethoxyphenylacetone represented by From the step of reacting with and reducing the reaction solution, the formula (III):

[0017]

[Chemical 10]

(R) -1- of the formula (III), which comprises a step of collecting (R) -1- (3,4-dimethoxyphenyl) -2-propanol of the formula
It relates to a method for producing (3,4-dimethoxyphenyl) -2-propanol.

[0019]

Examples Microorganisms that can be used in the present invention include the genus Ambrosiozyma, the genus Ashbya,
The genus Butryoascus, Candida
dida genus, Cryptococcus genus, Clavispora genus, Debaryomyce
s) genus, Dipodascus (Dipodascus) genus, Filobasidium (Filobasidium) genus, Geotrichum (Geotrichum) genus,
Guilliermondella genus, Williopsis genus, Kluyveromyc
es) genus, Lipomyces genus, rodaromyces
(Lodderomyces) genus, Meshschnikowia
Genus, Pachysolen genus, Pichia genus, Rhodosporidium genus, Cystofilobasidium genus, Rhodotorula (R
hodotorula), Saccharomyces
Genus, Yarrowia, Saccharomycopsis
charomycopsis), Schwanniomyce
s) genus, Schizosaccharomyces
Genus, Sporidiobolus genus, Sporobolomyces genus, Sterigmatomyces (S
terigmatomyces) genus, Torulaspora genus,
The genus Trigonopsis, Trichosporon (Tri
genus chosporon, genus Wickerhamia, genus Wingea, Zygosaccharus
omyces) genus, Alcaligenes (Alcaligenes) genus, Arthrobacter (Arthrobacter) genus, Bacillus (Bacillus) genus,
Micrococcus genus, Nocardia
Examples thereof include microorganisms belonging to the genus dia, the genus Pseudomonas, and the genus Rhodococcus.

Among these microorganisms, (S) -1- (3,4
In order to obtain -dimethoxyphenyl) -2-propanol, Ambrosiothyma spp, Candida spp, Cryptococcus spp, Clavispora spp, Devariomyces spp, Dipoduscus spp, Philobasidium spp, Geotricham spp, Guilliermondera spp, Willi Opsis, Kluyveromyces, Lipomyces, Meschenicobia,
Pachysolene, Pichia, Rhodosporidium, Kistophilobasidium, Rhodotorula, Saccharomyces, Yalobia, Saccharomycopsis, Schwaniomyces, Schizosaccharomyces, Spori de Oboras, Sporoboromy Ces, sterigmatomyces, toluraspora, trichosporon, wickerahamia, wingea, digosaccharomyces, alcaligenes, arthrobacterium, bacillus, micrococcus, nocardia, pseudomonas and rhodococcus Used. Specifically, Ambrosiozyma Philentoma (Ambrosiozym
a philentoma) IFO 1847, Ambrosiozyma platypodis IFO 1471, Candida glabrata IFO 0622, Candida glaebosa IFO 1353,
Candida guilliermondi
i) IFO 0454, Candida humicola
icola) CBS 2822, Candida magnolia
agnoliae) IFO 0705, Candida Maltosa (Candi
da maltosa) IAM 12247, Can da maltosa
dida maltosa) IFO 1977, Candida maltosa (C
andida maltosa) IFO 1978, Candida Maris
dida maris) IFO 1003, Candida Parapsilosis
(Candida parapsilosis) IFO 1022, Candida rugosa IFO 0591, Candida salmon (C
andida sake) CBS 2225, Candida s
ake) CBS 5740, Candida sake IFO
1517, Candida tropicali
s) IFO 0587, Candida uti
lis) IFO 0639, Candida u
tilis) IFO 0619, Candida Fersatiris (Candi
da versatilis) IFO 1228, Candida Giranoides
(Candida zeylanoides) IFO 0738, Candida albicans IFO 0759, Candida
Candida saitoana IFO 0380, Candida fennica CBS 6087, Cryptococcus albidus IFO 0378, Cryptococcus curvatus I
FO 1159, Cryptococcus humicorus
cus humicolus) IFO 0760, Cryptococcus humicolus JCM 1460, Cryptococcus laurentii IFO 060
9.Cryptococcus terreu
s) IFO 0727, Clavispora lu
sitaniae) IFO 1019, Debaryomyces Hansenny
Variety Hansenii (Debaryomyces hansenii va
r. hansenii) IFO 0032, Debaryomyces hansenii IFO 0063, Debaryomyces marama IFO 0668, Debaryomyces nepalensis IFO
0039, Dipodascus ge
otrichum) CBS 178,71 Dipoduscus magnusi (Dip
odascus magnusii) CBS 164,32, Dipodascus ovetensis IFO 1201, Dipodascus reessii CBS 179,60, Filobasidium capsulgenum (Filobasidium capsul)
igenum) IFO 1119, Geotricum Candy Dam (Geo
trichum candidum) CBS 187,67, Geotrichum eriense ATCC 22311, Geotricum
Fermentans (Geotrichum fermentans) CBS 2264,
Guilliermondellas
elenospora) IFO 1850, Williopsis suaveolens IFO 0809, Kluyveromyces marxianus IFO 028
8.Kluyveromyces Marchianus
marxianus) IFO 0541, Lipomyces starkei (Lip
omyces starkeyi) IFO 0678, Metschnikowia bicuspidata IFO 1408, Metschnikowia pulcherrima I
FO 0561, Metschnikow
ia reukaufii) IFO 0749, Paxolene tannophilus
(Pachysolen tannophilus) IFO 1007, Pichia anomala IFO 0707, Pichia capsulata (P
ichia capsulata) IFO 0721, Pichia Horsty (Pichi
a holstii) IFO 0980, Pichia minuta var.nonferme
ntans) IFO 1473, Pichia bovis IFO
0872, Pichia burtonii IFO 0844
, Pichia carsonii IFO 0946,
Pichia carsonii IFO 0795, Pichia farinosa IFO 0534, Pichia farinosa IFO 0462, Pichia carinii
Pichia farinosa IFO0991, Pichia membranaefaciens I
AM 4258, Pichia Membrana Efaciens (Pichi
a membranaefaciens) IFO 0180, Pichia pastoris (P
ichia pastoris) IFO 0948, Rhodosporidium dacryoidum IFO 1930,
Rhodospor
idium sphaerocarpum) IFO 1438, Rhodosporidium toruloides IFO 0559
, Cystofilobasidium infirmo-miniatum IFO 1378,
Rhodotorula araucariae
IFO 10053, Rhodotorula gl
utinis) IFO 0395, Rhodotorula glutinis var.dai
renensis) IFO 0415, Lord Torla Lactosa (Rhodo
torula lactosa) IFO 1423, Lord Torla Minuta
(Rhodotorula minuta) IFO 0928, Rhodotorula minuta IFO 0715, Rhodotorula rubra IFO 0383, Saccharomyces cerevisiae IFO 0206,
Saccharomyces cerevis
iae) IFO 0735, Yarrowia lipoly
tica) IFO 0746, Yarrowia lipo
lytica) IFO 1659, Saccharomycopsis maranga (S
accharomycopsis malanga) IFO 1710, Shubaniomyces occidentalis Variety occidentalis (Sch
wanniomyces occidentalis var. occidentalis) IFO 184
0, Schizosaccharomys pombe
ces pombe) IFO 0347, Sporidiobolus johnsonii IFO 6903, Sporobolomyces pararoseus IFO
0471, Sporoboromyces salmoni color (Sporobo
lomyces salmonicolor) IAM 12249, Sterigmatomyces halophilus IFO 14
88, Torulaspora delbr
ueckii) IFO 0381, Trichosporon Beigely (Trich
osporon beigelii) ATCC 22310, Trichosporon cutaneum IFO 1198, Trichosporon loubieri CBS 252,61
, Wickerhamia fluorescens (Wickerhamia fl
uorescens) IFO 1116, Wingea Roberts
robertsii) IFO 1277, Zygosaccharomyces bailii IFO 0488, Zygosaccharomyces rouxii IFO
0493, Alcaligenes sp. I
FO 14130, Arthrobacter Viscosus (Arthrobacte
r viscosus) IFO 13497, Bacillus amyloliquefaciens IFO 3022, Micrococcus roseus IFO 3768, Nocardia mexicana IFO 392
7, Pseudomonas cariophylly (Pseudomonas car
yophylli) IFO 12950, Rhodococcus erythropolis (R
hodococcus erythropolis) IFO 12320, Rhodococcus
Examples include Equi (Rhodococcus equi) JCM 1313.

On the other hand, in order to obtain (R) -1- (3,4-dimethoxyphenyl) -2-propanol, Ashivia, Butrioascus, Candida, Rodaromyces, Pichia, Rhodotorula, Trigonopsis are available. And those of the genus Pseudomonas are used. Specifically, Ashbya gossypii IFO 056
0, Butrio Ascus Cinna Edendras (Botryoasc
us synnaedendrus) IFO1604, Candida intermedia IFO 0761, Candida parapsilosis IFO 0640, Candida rugosa IFO 0750, Lodderomyces elongisp
orus) IFO 1676, Pichia haplop
hila) IFO0947, Road Torla Aurancia (Rhodot
orula aurantiaca) IFO 0754, Trigonopsis variabilis IFO 0671, Pseudomonas diminuta IFO 12697,
Pseudomonas riboflavi
na) IFO 13584 etc.

For culturing the above-mentioned microorganism, a medium containing a nutrient component generally used for culturing the microorganism (solid medium such as agar medium or liquid medium) can be used. A liquid medium is preferable for large-scale culture. The medium is glucose, sucrose, saccharides such as maltose as a carbon source, lactic acid, acetic acid, organic acids such as citric acid, alcohols such as ethanol and glycerol or a mixture thereof, and ammonium sulfate as a nitrogen source, ammonium phosphate, Urea, yeast extract, meat extract, peptone and the like are used. Furthermore, nutritional sources such as other inorganic salts and vitamins may be appropriately mixed. The microorganism can be cultured under normal conditions. For example, at pH 4.0 to 9.5, 20
It culture | cultivates aerobically in the temperature range (degreeC-45 degreeC) for 10-45 hours.

The substrate 3,4-dimethoxyphenylacetone is commercially available from Tokyo Chemical Industry Co., Ltd. In order to allow the microorganisms to act on the 3,4-dimethoxyphenylacetone, the culture solution of the microorganisms can be usually used as it is for the reaction, but if the components in the culture adversely affect the reaction, the culture is performed. A suspension of bacterial cells obtained by centrifuging the liquid may be used. The substrate may be added all at once at the initial stage of the reaction, or may be added in portions. The reaction temperature is usually 15 to 50 ° C,
The temperature is preferably 20 to 40 ° C., and the pH during the reaction is 2.5.
~ 9.0. The amount of the bacterial cells in the reaction solution may be appropriately used depending on the contact ability of the bacterial cells in the reaction. The substrate concentration is preferably 0.01 to 20% (w / v), more preferably 0.1 to 10% (w / v). The reaction is usually carried out with shaking or aeration and stirring. The reaction time is appropriately determined depending on the substrate concentration, the amount of microorganisms, and other reaction conditions. Usually, it is desirable to set each condition so that the reaction is completed in 2 to 168 hours. In order to promote the above reaction, excellent results are often obtained when glucose or the like is added to the reaction solution as an energy source at a ratio of 1 to 5%. As a result, the substrate 3,4-
Dimethoxyphenylacetone is an optically active 1- (3,
It is reduced to 4-dimethoxyphenyl) -2-propanol.

In order to collect the produced optically active 1- (3,4-dimethoxyphenyl) -2-propanol from the reaction solution, a general isolation method can be adopted. For example, an organic solvent such as ethyl acetate is added to the reaction solution for extraction. The obtained extract is dehydrated with anhydrous sodium sulfate or the like, and the organic solvent is removed under reduced pressure. As a result, the optically active 1-
A (3,4-dimethoxyphenyl) -2-propanol crude product can be obtained. Furthermore, if this crude product is purified by silica gel chromatography or the like, highly pure optically active 1- (3,4-dimethoxyphenyl) -2-
Can get propanol.

Next, the present invention will be described in more detail with reference to examples. However, these examples do not limit the scope of the present invention.

Example 1 A liquid medium having the following composition was prepared and placed in a large test tube.
Each 0 ml was dispensed and steam sterilization was performed at 120 ° C. for 20 minutes.

Medium composition: (per liter of tap water) Glucose 40 g Yeast extract 3 g (NH ₄ ) ₂ HPO ₄ 13 g KH ₂ PO ₄ 7 g MgSO ₄ .7H ₂ O 0.8 g ZnSO ₄ .7H ₂ O 0.07 g FeSO _{4 · 7H 2 O 0.09g CuSO 4} · 5H 2 O 0.005g MnSO 4 · 4H 2 O 0.01g NaCl 0.1g pH7.0 loopful inoculated microorganisms shown in tables 1 to 4 to these liquid medium Then, the cells were shake-cultured at 30 ° C. for 24-72 hours. Next, each culture solution is centrifuged to collect bacterial cells,
It was suspended in 5 ml of a phosphate buffer (pH 6.5) and used as the following reaction solution components.

Reaction liquid composition: (1) 5 ml of the above-mentioned bacterial cell suspension (2) Glucose 0.1 g (3) 3,4-dimethoxyphenylacetone 25 mg The above (1) to (3) were dispensed into a test tube. And mixed with each other, and reacted at 30 ° C. for 24 to 72 hours while shaking. After the reaction,
Ammonium sulfate was added to each reaction solution to saturate, 5 ml of ethyl acetate was added and mixed, and then the cells and the ethyl acetate layer were separated by centrifugation.

The obtained ethyl acetate layer was subjected to gas chromatography (column: 2 m glass column, packing material: silicone OV-210 20% 80/100 uniport HP, column temperature: 250 ° C., carrier gas: The residual amount of the substrate and the amount of the product were measured by N ₂ 1 kg / cm ² ). From the results, conversion rates to products were calculated and shown in Tables 1 to 4. Also, the optical purity (%
e. To determine e), the ethyl acetate layer was used to tosylate the hydroxyl groups of the product as follows. That is, the obtained ethyl acetate layer was subjected to solvent removal under reduced pressure, 0.15 ml of pyridine and 35 mg of tosyl chloride were added, and the mixture was stirred at room temperature for 1 to 5 hours. 2N hydrochloric acid 2m
1 was added to stop the reaction, and 2 ml of ethyl acetate was added for extraction. HPLC of the obtained ethyl acetate layer
(Column: CHIRALPAK AS 0.46 × 2
5 cm (manufactured by Daicel Chemical Industries, Ltd.), eluent: n-hexane / 2-propanol = 1/1, flow rate 1 ml / min,
The detection wavelength: 254 nm) was used to measure the optical purity (% ee) of the tosyl compound. From the results, the optical purities of the obtained optical metabolites are shown in Tables 1 to 4.

[0030]

[Table 1]

[0031]

[Table 2]

[0032]

[Table 3]

[0033]

[Table 4]

Example 2 A liquid medium having the composition shown in Example 1 was prepared and
Put 3000ml into a 00ml mini jar and
Steam sterilization was performed at 20 ° C. for 20 minutes (glucose was sterilized separately). Add the same composition medium 50 to the Sakaguchi flask.
Cryptococcus shaken in 30 ml at 30 ° C for 24 hours
Carbatus IFO 1159 was inoculated in the whole amount,
Cultured for 8 hours (450 rpm, 0.5 VVM, pH
Control the lower limit at 5.5). After completion of culture, culture solution 2
000 ml was adjusted to pH 6.5, 40 g of glucose and 14 g of 3,4-dimethoxyphenylacetone were added, and the microbial cell reaction was performed again using the same mini jar (30 ° C.,
20 hours, 450 rpm, 0.5 VVM, pH6.
5). After completion of the reaction, with the same amount of ethyl acetate as the reaction solution, the remaining 3,4-dimethoxyphenylacetone and the produced (S) -1- (3,4-dimethoxyphenyl) -2-
The propanol was extracted twice. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a solid substance. This solid substance was dissolved in a small amount of the following elution solvent and subjected to silica gel column chromatography (Merck).
CK) Silica gel 60 500 g, elution solvent: n-hexane / ethyl acetate = 2/1), and optical purity 99.0% e. e. (S) -1-
11.39 g of white crystals of (3,4-dimethoxyphenyl) -2-propanol were obtained. Obtained (S) -1-
Of (3,4-dimethoxyphenyl) -2-propanol
¹ H-NMR (400 MHz, CDCl ₃ ) and [α] D ²⁵ measured values are as follows. However, the optical purity (% ee) was measured by the same method as in Example 1.

¹ H-NMR (400 MHz CDCl ₃ ): δ: 6.74 to 6.84 (m, 3H), 3.9 to 4.0 (m, 1H), 3.88 (s, 3H), 3.
87 (s, 3H), 2.76 (dd, J = 4.4,13.7Hz, 1H), 2.61 (dd, J = 8.1,
13.5Hz, 1H), 1.26 (d, J = 5.86Hz, 3H) [α] D ²⁵ =; +30.5 (C = 1.01 CHCl ₃ ) Example 3 A liquid medium having the composition shown in Example 1 was prepared. , 50
50 ml was put into a 0 ml Sakaguchi flask and steam sterilized at 120 ° C. for 20 minutes. All of this was inoculated with Ashibia gossypii IFO 0560, which was shaken in a large-sized test tube in 5 ml of the same composition medium at 30 ° C for 24 hours, and then inoculated at 24 ° C at 30 ° C.
Cultured for hours. After the completion of the culture, the culture solution was adjusted to pH 6.5, glucose 1 g and 3,4-dimethoxyphenylacetone 0.5 g were added, and the bacterial cell reaction was performed again in the same Sakaguchi flask (30 ° C., 48 hours). After completion of the reaction, the same amount of ethyl acetate as the reaction solution left 3,4-dimethoxyphenylacetone and (R) -1- (3,4) produced.
-Dimethoxyphenyl) -2-propanol was extracted twice. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a solid substance. This solid substance was dissolved in a small amount of the following elution solvent and subjected to silica gel column chromatography (Merck silica gel 60 25).
g, elution solvent: n-hexane / ethyl acetate = 2/1), and the optical purity was 97.0% e.p. e. (R)-
0.40 g of white crystals of 1- (3,4-dimethoxyphenyl) -2-propanol was obtained. Obtained (R) -1-
Of (3,4-dimethoxyphenyl) -2-propanol
¹ H-NMR (400 MHz CDCl ₃ ) and [α]
The measured values of D ²⁵ are as follows. However, the optical purity (% ee) was measured by the same method as in Example 1.

¹ H-NMR (400 MHz CDCl ₃ ): δ: 6.74 to 6.84 (m, 3H), 3.9 to 4.0 (m, 1H), 3.88 (s, 3H), 3.
87 (s, 3H), 2.76 (dd, J = 4.4,13.7Hz, 1H), 2.61 (dd, J = 8.1,
13.5Hz, 1H), 1.26 (d, J = 5.86Hz, 3H) [α] D ²⁵ =; -29.7 (C = 1.01 CHCl ₃ )

[0037]

According to the present invention, the specific microorganisms are
Optically active 1- (3,4-dimethoxyphenyl) -by acting on dimethoxyphenylacetone
It becomes possible to efficiently produce 2-propanol on an industrial scale.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display part (C12P 7/02 C12R 1:74) (C12P 7/02 C12R 1:84) (C12P 7/02 C12R 1: 865) (C12P 7/02 C12R 1: 725) (C12P 7/02 C12R 1:05) (C12P 7/02 C12R 1:06) (C12P 7/02 C12R 1:07) (C12P 7/02 C12R 1: 265) (C12P 7/02 C12R 1: 365) (C12P 7/02 C12R 1:38)

Claims (2)

[Claims] 1. Formula (I): In 3,4-dimethoxyphenylacetone represented by, genus Ambrosiothyma, genus Candida, genus Cryptococcus, genus Clavispora, genus Devariomyces, genus Dipoduscus, phyllobasidium, genus Geotricum, genus Guilliermondera, genus Williopsis , Kluyveromyces, Lipomyces, Meschenicobia, Pachysolene, Pichia, Rhodesporidium, Kistophilobasidium, Rhodotorula, Saccharomyces, Yarovia, Saccharomycopsis, Shubaniomyce Genus Cess, Schizosaccharomyces genus, sporideoboras genus, sporoboromyces genus, Sterigmatomyces genus, Torulaspora genus, Trichosporon genus, Wickerahamia genus, Wingea, Digosaccharomyces genus, Alcaligenes, ar From the step of reacting and reducing a microorganism selected from the group consisting of microorganisms belonging to the genera Lobacter, Bacillus, Micrococcus, Nocardia, Pseudomonas and Rhodococcus, and from the reaction solution, the formula (II): ] A step of collecting (S) -1- (3,4-dimethoxyphenyl) -2-propanol represented by
A process for producing (S) -1- (3,4-dimethoxyphenyl) -2-propanol represented by the formula (II). 2. Formula (I): The 3,4-dimethoxyphenylacetone represented by is treated with a microorganism selected from the group consisting of microorganisms belonging to the genera Ashivia, Butrioascus, Candida, Rodaromyces, Pichia, Rhodotorula, Trigonopsis and Pseudomonas. From the reducing step and the reaction solution, the compound of the formula (III): (R) -1- (3,4-dimethoxyphenyl) -2-propanol represented by
A method for producing (R) -1- (3,4-dimethoxyphenyl) -2-propanol represented by the formula (III).