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Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. DOI: PubMed ID:

Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

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Product Details of [ 936-59-4 ]

CAS No. :936-59-4 MDL No. :MFCD00000990
Formula : C9H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :KTJRGPZVSKWRTJ-UHFFFAOYSA-N
M.W : 168.62 Pubchem ID :70295
Synonyms :
β-Chloroethyl phenyl ketone

Calculated chemistry of [ 936-59-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.24
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.53 mg/ml ; 0.00315 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 0.984 mg/ml ; 0.00583 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.029 mg/ml ; 0.000172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 936-59-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 936-59-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 936-59-4 ]
  • Downstream synthetic route of [ 936-59-4 ]

[ 936-59-4 ] Synthesis Path-Upstream   1~38

  • 1
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Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1330,1335
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 1541,1544
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Reference: [1] Journal of Organic Chemistry, 1951, vol. 16, p. 1541,1544
  • 3
  • [ 936-59-4 ]
  • [ 42142-52-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862
[3] Chinese Journal of Chemistry, 2011, vol. 29, # 3, p. 504 - 510
[4] Letters in Drug Design and Discovery, 2011, vol. 8, # 3, p. 268 - 275
  • 4
  • [ 18776-12-0 ]
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YieldReaction ConditionsOperation in experiment
93% With dihydrogen peroxide; acetic acid; sodium bromide In water at 60℃; for 2 h; Inert atmosphere General procedure: Under nitrogen atmosphere, to a solution of substrate alcohol (0.5 mmol) in aceticacid (1.0 mL) was added a stock-solution of aqueous NaBr solution (1.94 M, 25 μL)and 30percent aqueous H2O2 (50 μL, 0.5 mmol). After stirring the mixture for one hour at60 °C, additional 30percent aqueous H2O2 (50 μL, 0.5 mmol) was added, and stirring wascontinued for another one hour. After cooling, the mixture was poured into a saturatedaqueous NaHCO3 solution (ca. 30 mL) with the aid of CH2Cl2, and resulting mixturewas extracted with CH2Cl2. The combined organic layers were dried over anhydrousMgSO4, filtered and concentrated in vacuo. The residue was chromatographed onsilica gel (flash column or preparative TLC) to afford the corresponding ketone.
Reference: [1] Synlett, 2016, vol. 27, # 5, p. 789 - 793
[2] Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 323 - 326[3] Zhurnal Organicheskoi Khimii, 1969, vol. 5, # 2, p. 337 - 340
  • 5
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YieldReaction ConditionsOperation in experiment
100% With aluminum (III) chloride In dichloromethane at 0 - 20℃; Inert atmosphere 3-Chloropropionyl chloride (0.151 g; 1.19 mmol) followed by anhydrous benzene (0.084 g; 1.08 mmol) were added in a dropwise fashion to a solution of aluminum trichloride(0.173 g; 1.30 mmol) dissolved in anhydrous CH2CI2 (1 ml_), under N2 atmosphere at 0°C. The reaction mixture was allowed to warm to room temperature and left overnight.The reaction mixture was then cooled to 0°C and quenched by lumps of ice. The aqueous phase was extracted with CH2CI2 and the combined organic phases were dried over MgS04, filtered and concentrated. The product was purified by column chromatography (pentane) and isolated as yellow crystals in quantitative yield (0.200 g;1.19 mmol).Rf (pentane) 0.31. Mp (uncorr.): 45.9-48.7°C. 1H-NMR (400 MHz, CDCI3) δΗ 8.00-7.93 (m, 2H), 7.64-7.55 (m, 1 H), 7.53-7.44 (m, 2H), 3.93 (t, 2H, J 6.8 Hz), 3.46 (t, 2H, J 6.8 Hz). 13C-NMR (100 MHz, CDCI3) 5C 196.8, 136.5, 133.7, 128.9, 128.2, 41.4, 38.8. The NMR data are in accordance with those previously reported (Moriyama, K.;Takemura, M.; Togo, H. Org. Lett. 2012, 14, 2414-2417).
21 g With aluminum (III) chloride In benzene at 0 - 5℃; for 8 h; To a solution of 3-chloropropanoic acid (17.5 g, 189.8 mmol) in benzene (100 mL) was added thionyl chloride (45.2 g, 379.6 mmol, 28 mL) at room temperature. The resulting mixture was heated at 80-90°C for 4h. Excess thionyl chloride was removed by azeotropic distillation with dry benzene. 3-Chloropropionyl chloride thus obtained was diluted with benzene (150 mL). Anhydrous aluminum chloride (45 g, 340.0 mmol) was added slowly into flask over a period of 6h at 0-5°C under stirring. The reaction mixture was further stirred at 0-5°C for 2h. Excess aluminum chloride was decomposed carefully in ice-water and the reaction mixture was extracted with ethyl acetate (30 mL x 3). Combined organic layer was washed with water (10 mL x 5) to neutral pH and dried over sodium sulfate. Sodium sulfate was filtered off, washed with ethyl acetate (10 mL x 2) and the filtrate was concentrated under reduced pressure to give crude product, which was purified by column chromatography (5percent ethyl acetate/hexane) to provide 21.0 g of compound 2. Brown solid; Yield 69percent; Mp 46-49°C; IR (KBr): 3110, 2922, 1670 cm-1; ESI-MS: m/z 169 (M++1),171 (M++3); 1H NMR (300 MHz, CDCl3): d 7.93-7.91 (m, 2H), 7.64-7.38 (m, 3H), 3.88 (t, 2H, J = 6.9 Hz), 3.41 (t, 2H, J = 6.9 Hz); Anal. calcd. for C9H9ClO: C, 64.11; H, 5.38; Found: C, 64.12; H, 5.34.
Reference: [1] Patent: WO2013/26455, 2013, A1, . Location in patent: Page/Page column 74
[2] Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 285 - 291
[3] Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 285 - 291
[4] Organic Preparations and Procedures International, 1997, vol. 29, # 2, p. 214 - 218
[5] Pharmaceutical Research, 2017, vol. 34, # 12, p. 2873 - 2890
[6] Chirality, 2012, vol. 24, # 10, p. 847 - 853,7
[7] Journal of the Chemical Society, 1935, p. 299,301[8] Chemische Berichte, 1936, vol. 69, p. 16,17
[9] Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 645 - 649
[10] Journal of Organic Chemistry, 1949, vol. 14, p. 346,349
[11] Journal of the American Chemical Society, 1932, vol. 54, p. 736,747
[12] Journal of Organic Chemistry, 1972, vol. 37, p. 1494 - 1499
[13] Archiv der Pharmazie, 1962, vol. 295 /67, p. 241 - 243
[14] Journal of the American Chemical Society, 1965, vol. 87, p. 1515 - 1521
[15] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 3924 - 3926
[16] Tetrahedron Asymmetry, 2008, vol. 19, # 9, p. 1078 - 1083
[17] Journal of Medicinal Chemistry, 2008, vol. 51, # 13, p. 3841 - 3855
[18] Patent: WO2008/35358, 2008, A2, . Location in patent: Page/Page column 8; 9-10
[19] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 176 - 181
[20] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3262 - 3272
[21] Russian Journal of Bioorganic Chemistry, 2015, vol. 41, # 1, p. 37 - 45[22] Bioorg. Khim., 2015, vol. 41, # 1, p. 44 - 53,10
[23] Organic and Biomolecular Chemistry, 2016, vol. 14, # 16, p. 3883 - 3888
  • 6
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YieldReaction ConditionsOperation in experiment
90 %Chromat. With iron(III) chloride; tetraphenylsilane In <i>tert</i>-butyl alcohol at 80℃; for 24 h; In a 25 mL reaction flask, ferric chloride (0.05 mmol), ene 1ag (0.5 mmol), tetraphenyl disilane (2.0 mmol) and tert-butanol (2.0 mL) were added successively to the 25 mL reaction flask.After mixing at room temperature, the reaction mixture was reacted at 80 ° C for 24 h.The reaction was completed, aqueous ammonia (0.5 mL) was added and stirred for 1 h.Then, 5 mL of water was added and extracted with ether (5 mL x 3). The organic phases were combined and the solvent was evaporated under reduced pressure. Column chromatography gave 90percent yield.
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12712 - 12717[2] Angew. Chem., 2017, vol. 129, p. 12886 - 12891,6
[3] Patent: CN106748690, 2017, A, . Location in patent: Paragraph 0124; 0125; 0126
  • 7
  • [ 104-52-9 ]
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Reference: [1] Organic Letters, 2012, vol. 14, # 9, p. 2414 - 2417
  • 8
  • [ 768-03-6 ]
  • [ 936-59-4 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6430 - 6433
[2] American Chemical Journal, 1909, vol. 42, p. 393
  • 9
  • [ 93-55-0 ]
  • [ 936-59-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 6, p. 1266 - 1274
  • 10
  • [ 18776-12-0 ]
  • [ 936-59-4 ]
  • [ 100306-33-0 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6495 - 6497
  • 11
  • [ 625-36-5 ]
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Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 957,962
  • 12
  • [ 98-88-4 ]
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Reference: [1] Canadian Journal of Research, 1933, vol. 8, p. 440,444
  • 13
  • [ 2674-04-6 ]
  • [ 625-36-5 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1984, vol. 2, # 7-8, p. 285 - 291
  • 14
  • [ 623-71-2 ]
  • [ 936-59-4 ]
  • [ 24626-27-5 ]
Reference: [1] Journal of the Chemical Society, 1936, p. 401
  • 15
  • [ 50-00-0 ]
  • [ 98-86-2 ]
  • [ 936-59-4 ]
  • [ 39192-57-9 ]
  • [ 54589-56-9 ]
  • [ 768-03-6 ]
Reference: [1] Russian Journal of General Chemistry, 2007, vol. 77, # 4, p. 611 - 619
  • 16
  • [ 60-29-7 ]
  • [ 623-71-2 ]
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  • [ 24626-27-5 ]
Reference: [1] Journal of the Chemical Society, 1936, p. 401
  • 17
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YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; ethanol In tetrahydrofuran at -10 - -5℃; for 0.333333 h; Inert atmosphere To a stirred solution of 3-chloro-1 -phenylpropan-1 -one (7.80 g, 46.26 mmol) in THF (35 mL) and EtOH (35 mL), at -10 °C and under a nitrogen atmosphere, sodium borohydride (2.20 g, 48.83 mmol) was added portion-wise over 10 min. The reaction mixture was stirred for additional 10 min at -5 °C then cautiously poured into a stirred mixture of saturated ammonium chloride (85 mL) and ice (40 g). The mixture was extracted with ether twice, the organic phase was dried and the solvent removed under reduced pressure. The crude material was purified by FC on silica gel (eluting with Cy/EA from 100/0 to 95/5) to give the title compound 3-chloro-1 -phenylpropan-1 -ol (p281 , 7.50 g, y= 95percent) as pale yellow oil. NMR: 1 H NMR (CDC ) δ: 7.39 (d, 5H), 4.91 -5.01 (m, 1 H), 3.70-3.83 (m, 1 H), 3.59 (s, 1 H), 2.20-2.32 (m, 1 H), 2.1 1 (d, 1 H)
83.1%
Stage #1: With (S)-1-Pyrrolidin-2-yl-methanol In ethanol at 35 - 40℃; for 0.25 h;
Stage #2: With potassium borohydrite In ethanol for 2 h; Reflux
Take 5600 ml of 95percent ethanol, add to a 10 L reaction bottle, and start stirring. Then, 800 g of 3-chloropropiophenone and 360 g of L-prolinol were sequentially added to the reaction flask, and stirred at 35-40 ° C for 15 minutes, until the reaction solution was almost completely dissolved.Cool to 27 ° C. Boron potassium hydride 320g was added to the reaction mixture in portions, and the addition speed was taken to prevent the gas from being generated in a large amount to cause the reaction liquid to expand and overflow. After the addition and the incubation reaction was carried out for 0.8 hours, the reaction solution was refluxed for 1.2 hours.The reaction solution was concentrated to 1.2 L under reduced pressure, and then added to 7870 ml of n-hexane, and heated to 55-60 ° C. After dissolved, 80 g of activated carbon was added, and the mixture was decolorized for 0.6 hours. The mixture was filtered while hot, and the filtrate was washed with 700 ml of n-hexane to collect filtrate. The mixture was decanted at 0-5 ° C for 1.3 hours, filtered, and the filter cake was rinsed once with 500 ml of n-hexane and dried under vacuum.White flocculent solid 3-chlorophenylpropanol 677g,The yield was 83.1percent.The HPLC content was 98percent and the ee value was 99percent.
82% With sodium tetrahydroborate In methanol at 0 - 20℃; for 2 h; To a solution of 3-chloropropiophenone (8.46 g, 50.0 mmol) in methanol (100 mL) wasadded NaBH4 (0.981 g, 25.9 mmol) at 0 °C and the mixture was warmed to roomtemperature with stirring for 2 h. HClaq (1 M, 100 mL) was added at 0 °C. Themixture was extracted with ethyl acetate (2 x 100 mL) and washed with water (2 x 150mL). The combined organic layer was dried over MgSO4 and evaporated. The residuewas purified by distillation under reduced pressure to give the product (6.99 g, 82percent).The spectral data were exactly matched to the reported data.30
16.5 g at 0 - 15℃; for 2 h; In 250mlAdd 15.97g in a three-necked flask3-chloropropiophenone and methanol 120ml, At 0 ~ 5 3.87g KBH4 was added in portions,The temperature of the reaction mixture is controlled within the range of 0 to 5 ° C.,Then control the temperature at 5 ~ 15 for 2 hours,Methanol was evaporated under reduced pressure, 80 ml of water was added, and the mixture was extracted with 50 ml of ethyl acetate * 3. The combined organic layers were dried and the organic layer was dried. Ethyl acetate was distilled off under reduced pressure at 50 ° C,3-chlorophenyl propanol 16.5g

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[2] Biological and Pharmaceutical Bulletin, 2011, vol. 34, # 4, p. 538 - 544
[3] Patent: WO2016/67043, 2016, A1, . Location in patent: Page/Page column 325
[4] Organic Process Research and Development, 2000, vol. 4, # 6, p. 513 - 519
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 11, p. 1767 - 1769
[6] Angewandte Chemie - International Edition, 2013, vol. 52, # 12, p. 3490 - 3493[7] Angew. Chem., 2013, vol. 125, # 12, p. 3574 - 3577,4
[8] Chinese Journal of Chemistry, 2011, vol. 29, # 3, p. 504 - 510
[9] Letters in Drug Design and Discovery, 2011, vol. 8, # 3, p. 268 - 275
[10] Patent: CN108383703, 2018, A, . Location in patent: Paragraph 0019; 0020; 0021
[11] Chemistry Letters, 2017, vol. 46, # 8, p. 1116 - 1118
[12] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862
[13] Journal of the Chemical Society, Chemical Communications, 1986, # 13, p. 1018 - 1019
[14] Journal of Chemical Research, Miniprint, 1987, # 12, p. 3242 - 3264
[15] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 12, p. 3197 - 3206
[16] Synthesis, 2011, # 18, p. 2921 - 2928
[17] Angewandte Chemie - International Edition, 2015, vol. 54, # 29, p. 8511 - 8514[18] Angew. Chem., 2015, vol. 54, # 29, p. 8511 - 8514,4
[19] Journal of the American Chemical Society, 1957, vol. 79, p. 948,950
[20] Journal of the American Chemical Society, 1933, vol. 55, p. 2927,2930
[21] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1969, p. 2113 - 2116[22] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1969, # 10, p. 2266 - 2269
[23] Journal of Medicinal Chemistry, 1999, vol. 42, # 16, p. 3101 - 3108
[24] Journal of the American Chemical Society, 1974, vol. 96, p. 7968 - 7974
[25] Tetrahedron Asymmetry, 1992, vol. 3, # 4, p. 525 - 528
[26] Tetrahedron, 1994, vol. 50, # 19, p. 5775 - 5782
[27] Bulletin de la Societe Chimique de France, 1994, vol. 131, # 6, p. 632 - 635
[28] Tetrahedron, 1997, vol. 53, # 15, p. 5563 - 5572
[29] Bioorganic and medicinal chemistry letters, 2003, vol. 13, # 7, p. 1291 - 1292
[30] Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5512 - 5532
[31] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 3924 - 3926
[32] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 589 - 593
[33] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6495 - 6497
[34] Journal of Medicinal Chemistry, 2008, vol. 51, # 13, p. 3841 - 3855
[35] Organic Letters, 2009, vol. 11, # 2, p. 305 - 308
[36] Patent: WO2008/35358, 2008, A2, . Location in patent: Page/Page column 8; 10
[37] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 176 - 181
[38] Organic Letters, 2011, vol. 13, # 10, p. 2762 - 2765
[39] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[40] Molecules, 2015, vol. 20, # 1, p. 1712 - 1730
[41] Russian Journal of General Chemistry, 2015, vol. 85, # 4, p. 922 - 925
[42] Synlett, 2016, vol. 27, # 5, p. 789 - 793
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[44] Synthesis (Germany), 2016, vol. 48, # 19, p. 3241 - 3253
[45] Patent: CN106748817, 2017, A, . Location in patent: Paragraph 0041; 0042; 0043
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  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
60 %Chromat. With yeast culture of Rhodotorula rubra KCh 82 In acetone at 25℃; for 6 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 94 - 98
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YieldReaction ConditionsOperation in experiment
94% With potassium formate In water; toluene at 50℃; for 24 h; 3.36 g (40.0 mmol) of HCOOK as the hydrogen source, 2.609 mg (4.0 μmol) of Cp*IrCl[(S,S)-MsDPEN] as the catalyst, and 1.349 g (8.0 mmol) of β-chloropropiophenone were introduced in a 20 mL Schlenk tube, and the mixture was subjected to argon substitution. 2 mL of water and 2 ml of toluene were added and the resulting mixture was maintained at 50° C. for 24 hr while stirring. The organic phase was washed three times with 3 mL of water, and the toluene was distilled off under reduced pressure to give an optically-active alcohol. GC analysis of the reactant confirmed that 3-chloro-1-phenylpropane-1-ol with optical purity of 85percent ee was produced in 94percent yield.
94% With dimethylsulfide borane complex; (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine In tetrahydrofuran at 20℃; for 2 h; Cat-6 (1.78 mmol, 575 mg) prepared in Preparation 2.6 was dissolved in 25 mL of THF, BH3-DMS (12.5 mmol, 1.18 mL) was added, and the mixture was stirred for about 7 minutes. To the reaction mixture was added dropwise a solution of 3-chloropropiophenone (17.8 mmol, 3.0 g) dissolved in 6 ml of THF dropwise over 10 minutes. After reacting at room temperature for 2 hours, the reaction was terminated by the addition of methanol. Example 1.1.(S) -3-chloro-1-phenyl-propanol (yield: 94percent, 91percent ee).The above compound was recrystallized from the nucleic acid to obtain (S) -3-chloro-1-phenyl-propanol (84percent recovery) with 99percent ee.
94% With dimethylsulfide borane complex; (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine In tetrahydrofuran at 20℃; for 2.16667 h; Cat-1 (1.78 mmol, 575 mg) prepared in Preparation 1.1 was dissolved in 25 mL of THF, BH3-DMS (12.5 mmol, 1.18 mL) was added, and the mixture was stirred for about 7 minutes. A solution of 3-chloropropiophenone (17.8 mmol, 3.0 g) in 6 mL of THF was added dropwise to the reaction mixture dropwise over 10 minutes. After reacting at room temperature for 2 hours, the reaction was terminated by the addition of methanol. After removal of the solvent, ethyl acetate and water were added to separate the organic layer. Ethyl acetate was added to the separated aqueous layer to further extract it. The organic layers were combined, dried over Na2SO4, and filtered. The obtained filtrate was concentrated and purified by column chromatography (hexane: ethyl acetate = 3: 1) to obtain (S) -3-chloro-1-phenylpropan-1-ol (yield: 94percent & Lt; / RTI & gt; The above compound was recrystallized in a nucleic acid to obtain (S) -3-chloro-1-phenylpropan-1-ol (84percent recovery) at 99percent ee.
79%
Stage #1: With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In toluene at 20℃; for 6 h; Inert atmosphere
Stage #2: With hydrogenchloride In methanol; water; toluene for 0.166667 h; Inert atmosphere
To a stirred solution of (R)-(+)-2-methyl-CBS-oxazaborolidine (29 mg, 0.107 mmol) in anhydrous toluene (3 mL) was added N,N-diethylaniline borane (0.63 mL, 3.558 mmol) at room temperature. 3-Chloropropiophenone (2) (0.3 g, 1.779 mmol) in anhydrous toluene (3 mL) was slowly added with the aid of a syringe pump over 5 h under N2. The reaction mixture was stirred for 1 h at room temperature. The reaction mixture was quenched with MeOH (1 mL) followed by addition of 1 N HCl (1 mL) and stirred for 10 min. The organic layer was separated and the aqueous layer was extracted with EtOAc (50 mL .x. 2). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc = 6:1) to afford 239 mg (79percent) of 3 as a white solid.Rf = 0.48 (n-hexane/EtOAc = 4/1); [α]22D -23.5 (c 0.1, CHCl3); IR (neat) ν 3060, 2878, 1620, 1612, 1596, 1452, 1215, 1190, 1042, 1020, 988 cm-1; 1H NMR (300 MHz, CDCl3) δ 1.92 (d, J = 3.3 Hz, 1H), 2.08-2.13 (m, 1H), 2.18-2.28 (m, 1H), 3.52-3.60 (m, 1H), 3.70-3.78 (m, 1H), 4.92-4.97 (m, 1H), 7.27-7.40 (m, 5H); 13C NMR (500 MHz, CDCl3) δ 41.7, 41.9, 71.6, 126.0, 128.1, 128.9, 143.9; HRMS (EI) Calcd for C9H11ClO [M+H]+ 170.0498, found 170.0500; HPLC (Chiralcel OD-H column, n-hexane:i-PrOH = 92:8, 1 mL/min, 210 nm): tmajor = 8.38 min, tminor = 9.87 min; ee > 99.9percent.
73% With (S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate In toluene at -20℃; for 24 h; Inert atmosphere; Schlenk technique Following a procedure recently reported by Wu and Li,25Cu(OAc)2·H2O (119.8 mg, 0.6 mmol) and (S)-P-Phos (151.4 mg, 0.2mmol) were weighed under air and dissolved in toluene (66 mL). The reaction mixture was stirred at r.t. for 20 min, then a solution of phenylsilane(3 mL, 24 mmol) in toluene (32 mL) was added. The mixturewas cooled to –20 °C and a solution of 3-chloro-1-propiophenone(13) (3.4 g, 20 mmol) in toluene (32 mL) was added under vigorous stirring. The flask was stoppered and the reaction mixture was stirred for 24 h at the above temperature. Upon completion, the mixture was treated with 10percent HCl (130 mL) and the organic product was extracted with Et2O (3 × 150 mL). The combined organic layers were washed with H2O, dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography on silica gel (hexane/EtOAc, 10:1)afforded alcohol (S)-23 (2.5 g, 73percent) as a white solid.The ee value was determined by chiral HPLC analysis with a Chiralcel IB column (eluent: hexane/2-propanol = 98:2; flow rate: 1 mL/min;detection: 254 nm), tR (R) = 16.2 min (areapercent 97), tR (S) = 18.1 min (areapercent3). Spectral data matched those previously reported for 23. Theoptical rotation matched literature data.32 [α]D27.4 –23 (c 1.0, CHCl3).
84 mg With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the medium consisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.

Reference: [1] Patent: US2009/62573, 2009, A1, . Location in patent: Page/Page column 7; 14
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 6, p. 1009 - 1017
[3] Patent: KR2015/116956, 2015, A, . Location in patent: Paragraph 0176-0179
[4] Patent: KR2016/44117, 2016, A, . Location in patent: Paragraph 0063-0066
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3854 - 3862
[6] Chirality, 2012, vol. 24, # 10, p. 847 - 853,7
[7] Tetrahedron Letters, 2012, vol. 53, # 28, p. 3680 - 3682
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4929 - 4931
[9] Synthesis (Germany), 2016, vol. 48, # 19, p. 3241 - 3253
[10] Tetrahedron Asymmetry, 2006, vol. 17, # 12, p. 1769 - 1774
[11] Journal of Organic Chemistry, 1988, vol. 53, # 13, p. 2916 - 2920
[12] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 11, p. 1767 - 1769
[13] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 11, p. 1767 - 1769
[14] Tetrahedron Asymmetry, 1992, vol. 3, # 4, p. 525 - 528
[15] Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14234 - 14240
[16] Journal of Molecular Catalysis B: Enzymatic, 2011, vol. 70, # 3-4, p. 114 - 118
[17] Chirality, 2012, vol. 24, # 10, p. 847 - 853,7
[18] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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YieldReaction ConditionsOperation in experiment
75% With dimethylsulfide borane complex; C23H22BNO3 In tetrahydrofuran at 20℃; for 2 h; Cat-5 (0.05 mmol, 20 mg) prepared in Preparation Example 2.5 was dissolved in 1 ml of THF, BH3-DMS (0.42 mmol, 0.04 ml) was added, and the mixture was stirred for about 7 minutes. A solution of 3-chloropropiophenone (0.6 mmol, 100 mg) in 0.45 ml of THF was added dropwise to the reaction mixture. After reacting at room temperature for 2 hours, the reaction was terminated by the addition of methanol. (R) -3-chloro-1-phenylpropanol (yield: 75percent, 73percent ee) was obtained in the same manner as in Example 1.1.
77 % ee With hydrogen In methanol at 60℃; for 24 h; 6.127 mg (8.0 μmol) of Cp*Ir(OTf)[(S,S)-MsDPEN] and 1.249 g (8.0 mmol) of β-chloropropiophenone were introduced in an autoclave, and the mixture was subjected to argon substitution. 3.3 mL of methanol was introduced and deaeration was performed, then hydrogen gas was introduced at 10 atm and the resulting mixture was maintained at 60° C. for 24 hr while stirring. The solvent was distilled off under reduced pressure to give a crude product. GC analysis of the reactant confirmed that 3-chloro-1-phenylpropane-1-ol with optical purity of 77percent ee was produced in 12percent yield. Comparison with Example E-1 demonstrated the superiority of the asymmetric reduction using a potassium formate solution as the hydrogen source.
80 % ee With dimethylsulfide borane complex; (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine In tetrahydrofuran at 20℃; for 1 h; General procedure: To a solution of 1 (0.005–0.01 mmol, 0.5–1 mol percent) in dry THF(3 mL) at room temperature, a solution of BH3SMe2 (10 M,100 lL, 1 mmol) in THF (2 mL) was added dropwise at a rate of3.2 mL per hour using a syringe pump. At the same time a solutionof ketone (1 mmol) in THF (2 mL) was also added to the reactionflask at a rate of 3 mL per hour. After the addition of both reagents,the reaction mixture was stirred for 20 min, quenched by the additionof MeOH (1 mL) at room temperature, and stirred for 30 min. Subsequently, the solvents were evaporated under vacuum and theproduct was isolated by column chromatography using hexane/EtOAc (4:1) as the eluent.
66 % ee at 20℃; for 20 h; General procedure: A flask was charged with azolium salt L12 (0.02 mmol, 9.1 mg),Ag2O (0.01 mmol, 2.4 mg) and CH2Cl2(1 mL). After stirring the resulting mixture at room temperature for 2 h in the dark, CH2Cl2 was removed in vacuo. Then, a THF (1 mL) solution of [IrCl(cod)]2(0.01 mmol, 6.9 mg) was added to the reaction vessel. The resulting mixture was stirred at room temperature for an additional 4 h in the dark, filtered through a membrane filter, and evaporated to dry-ness in vacuo. Subsequently, to the resulting flask containing yellow solid of the unpurified IrCl(cod)(NHC) complex, a solution of AgBF4(0.025 mmol, 4.9 mg) in CPME (2 mL) was added, and then stirred at room temperature for 1 h. Finally, propiophenone (0.5 mmol,66 mg) and (EtO)2MeSiH (2.25 mmol, 294 mg) were added to the resulting CPME solution (see Appendix A. Supplementary data fordetails). After stirring at room temperature for 20 h under open-air conditions, K2CO3(2 mg) and MeOH (2 mL) were added. Then, the resulting mixture was stirred at room temperature for 2 h. Afterevaporation of the solvents, the residue obtained was purified bycolumn chromatography on silica gel (Et2O/n-hexane = 3:7) to give(S)-1-phenyl-1-propanol (61 mg, 91percent isolated yield). The ee was measured by chiral GLC.

Reference: [1] Patent: KR2015/116956, 2015, A, . Location in patent: Paragraph 0143; 0154; 0155
[2] Tetrahedron Letters, 2005, vol. 46, # 3, p. 495 - 498
[3] Tetrahedron Letters, 1993, vol. 34, # 26, p. 4145 - 4148
[4] Journal of the Chemical Society, Chemical Communications, 1986, # 13, p. 1018 - 1019
[5] Tetrahedron, 2002, vol. 58, # 6, p. 1069 - 1074
[6] Tetrahedron Asymmetry, 2001, vol. 12, # 16, p. 2323 - 2329
[7] Organic Letters, 2006, vol. 8, # 14, p. 2969 - 2972
[8] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5799 - 5802
[9] Patent: US2009/62573, 2009, A1, . Location in patent: Page/Page column 8; 14
[10] Organic Letters, 2009, vol. 11, # 2, p. 305 - 308
[11] Organic Process Research and Development, 2012, vol. 16, # 4, p. 710 - 713
[12] Green Chemistry, 2014, vol. 16, # 5, p. 2680 - 2688
[13] Catalysis Letters, 2014, vol. 144, # 7, p. 1289 - 1295
[14] Chemistry - A European Journal, 2014, vol. 20, # 38, p. 12190 - 12200
[15] Tetrahedron Asymmetry, 2015, vol. 26, # 24, p. 1453 - 1458
[16] Organic and Biomolecular Chemistry, 2016, vol. 14, # 18, p. 4304 - 4311
[17] Journal of Molecular Catalysis A: Chemical, 2016, vol. 421, p. 138 - 145
[18] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 426 - 431
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YieldReaction ConditionsOperation in experiment
60.526 % ee at 28℃; for 48 h; Microbiological reaction; Enzymatic reaction General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h.
23 %Chromat. With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 6 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 94 - 98
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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YieldReaction ConditionsOperation in experiment
21 %Chromat. With yeast culture of Aphanocladium album KCh 417 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33 %Chromat. With yeast culture of Saccharomyces cerevisiae KCh 464 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33 %Chromat. With yeast culture of Saccharomyces pastorianus KCh 906 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[3] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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33 %Chromat. With yeast culture of Candida parapsilosis KCh 909 In acetone at 25℃; for 72 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
57 %Chromat. With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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61 %Chromat. With yeast culture of Saccharomyces brasiliensis KCh 905 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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21 %Chromat. With yeast culture of Rhodotorula rubra KCh 4 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 21, p. 6019 - 6023
[2] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 94 - 98
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Reference: [1] Catalysis Letters, 2014, vol. 144, # 7, p. 1289 - 1295
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Reference: [1] Tetrahedron Asymmetry, 2001, vol. 12, # 7, p. 1025 - 1034
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97% With borane-THF; (S)-diphenylprolinol In tetrahydrofuran; toluene at 20℃; for 1.5 h; Step 1: a flask was charged with (S)-(−)-α,α-diphenylprolinol (0.30 g, 1.19 mmol) and anhydrous toluene (7 ml). The mixture was placed under nitrogen by evacuation and filling three times. The borane tetrahydrofuran complex solution [BH3•THF; 1M solution in THF, stabilized with 5mM NaBH4] (0.35 ml, 3.56 mmol) was added in a dropwise fashion at 30°C and the clear solution was stirred for 30min. Step 2: to this stirred solution, 3-chloro-1-phenylpropan-1-one 12 (1 g, 5.93 mmol) in anhydrous toluene (1 ml) was added. The reaction mixture was then stirred at room temperature for 15min followed by the addition of BH3·THF (6 ml, 61.44 mmol) over a period of 3 min. After stirring for additional 9 0min, the reaction flask was cooled in ice bath and quenched successively with MeOH (10 ml), isopropanole (10 ml), and HCl (3 ml), and was passed through a pad of Celite. The filtrate was concentrated to dryness and crystallized from hexane. The title compound was obtained as white fluffy solid (4.91g). Yield: 97percent; m.p. 57–59°C; [α]D25=+ 25.7° (c 1, CHCl3); 1H NMR (400MHz, CDCl3): δ 2.07–2.16 (m, 2H), 2.20–2.32 (m, 1H), 3.51–3.62 (m, 1H), 3.71–3.80 (m, 1H), 4.91–4.98 (m, 1H), 7.37–7.43 (m, 5H), 13C NMR (400MHz, CDCl3): δ 41.45, 41.73, 71.34, 125.80, 127.94, 128.69, 143.71; MS (EI+) m/z: 170 [M+], 172 [M+2] showing relative intensity ratio∼3:1.
95% With 2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine; dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 2 h; Preparative Example 2.2. Dissolving the 2-cat (1.78 mmol, 575 mg) prepared inaccordance with the 25 of THF and, after the addition of BH3 DMS (12.5 mmol,1.18 ), which was stirred for 7 minutes. Over a solution of 3-chloro-propiophenone(17.8 mmol, 3.0 g) was dissolved in THF 6 to the reaction mixture was addeddropwise a 10 minute dropwise. After reacting at room temperature for an 2 hour, thereaction was terminated by adding methanol. Example 1.1. And purified in the samemanner as (R) -3- chloro-1-phenyl-propanol to give the (yield: 95percent, 93percent ee).The compound was recrystallized from a nucleic acid of 99percent ee (R) -3- chloro-1-phenyl-propanol to give the (86percent recovery).
95% With 2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine; dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 2.16667 h; Cat-2 (1.78 mmol, 575 mg) prepared in Preparation Example 1.2 was dissolved in 25 mL of THF, BH3-DMS (12.5 mmol, 1.18 mL) was added, and the mixture was stirred for about 7 minutes. A solution of 3-chloropropiophenone (17.8 mmol, 3.0 g) in 6 mL of THF was added dropwise to the reaction mixture dropwise over 10 minutes. After reacting at room temperature for 2 hours, the reaction was terminated by the addition of methanol. (R) -3-chloro-1-phenylpropan-1-ol (yield 95percent, 93percent ee) was obtained in the same manner as in Preparation Example 2.2. The above compound was recrystallized from a nucleic acid to obtain (R) -3-chloro-1-phenylpropan-1-ol (86percent recovery) with 99percent ee.
91% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; C55H92N6O4S(2+)*2I(1-); sodium formate In water A solution of 1.3 mg (0.002 mmol) metal [RhCl2Cp*]2 and 5.2 mg (0.004 mmol) ligand XIV is in the thick wall of the test tube, add 5 ml water placed in the 40 °C activation stirring 2 hours. 0.4 mmol 3-chlorophenylacetone and 2 mmol sodium formate, stirring the reaction. The solution was extracted with ethyl acetate 5 ml × 3 extraction, combined the organic phase, dried with anhydrous sodium sulfate, the solvent was evaporated. Column chromatography purification (petroleum ether / ethyl acetate = 20/1). HPLC detection ee value. For the product passes through the derivatization ee value detected: the obtained product is dissolved in 5 ml dichloromethane in, adding 49 mg 4-dimethylaminopyridine (0.4 mmol) and 82 mg of acetic anhydride (0.8 mmol), stir at room temperature 3h. Processing, dichloromethane is used for solution 5 ml × 3 extraction, the combined organic phase, dried with anhydrous sodium sulfate, the solvent, then the GC detection ee value. Isolation yield 91percent, 95percent ee
86% With dimethylsulfide borane complex In tetrahydrofuran for 2 h; EXAMPLE 8R-(+)-3-chloro-1-phenylpropan-1-olFollowing similar procedure as before, BH3.SMe2 (10 M, 0.7 mL, 7 mmol) was added to a solution of complex derived from ethylene glycol and diphenyl prolinol (EG-DDP), catalyst 10, (323 mg, 0.1 mmol) in dry THF (35 mL) at room temperature. The reaction mixture was stirred for approximately one hour. A solution of dry 3-chloropropiophenone (1.69 g, 10 mmol) in dry THF (5 mL) was added by a syringe using infusion pump for 1 hour. (Rate: 6 mL/h). The 3-chloropropiophenone solution was light yellow but after adding to the complex, the total solution was clear. Following similar procedure as above for the work-up, the crude product was obtained: 1.66 g (97percent yield). The product was analyzed by 31P-NMR: 145.0 ppm (5.7percent), 134.5 ppm (94.3percent)-->88.6percent ee. The product was purified by column chromatography with 30 g of silica and a mobile phase of hexane/ethyl acetate (2:1).(Yield: 1.47 g, 86percent). The product was analyzed by 1H, 13C, and 31P-NMR (derivative with a phosphonate (CDA). 31P-NMR: 145.1 ppm (3percent), 134.6 ppm (97percent): 94percent ee; [α]20=+21.0 c=0.030 (CHCl3).
86.7% With (+)-diiso-2-ethylapophosphate pinacylboraneheptane In tetrahydrofuran at -20℃; for 6 h; 3-Chlorophenylacetone (40 g) was dissolved in tetrahydrofuran (160 ml)(152 ml) of 65percent (+) diiso-2-ethylapopamate-pinacylborane n-heptane was added at -10 ° C,The reaction was carried out for 8 hours and concentrated under reduced pressure. The residue was added with diethyl ether (400 ml), followed by addition of diethanolamine (37.4 g), stirred for 2 h and filtered. (R) - (+) - 3-chlorophenyl propanol 7.4g, the yield was 86.7percent, mp56 ~ 57 (m), and the mixture was stirred at room temperature for 4 hours. ° C; [a] 23d = + 25.1, c = 1, CHC13; 99percent ee.
9% With hydrogen In methanol at 60℃; for 24 h; 5.010 mg (8.0 μmol) of RuCl[(R,R)-TsDPEN](p-cymene) and 1.249 g (8.0 mmol) of β-chloropropiophenone were introduced in an autoclave, and the mixture was subjected to argon substitution. 3.3 mL of methanol was introduced and deaeration was performed, then hydrogen gas was introduced at 10 atm and the resulting mixture was maintained at 60° C. for 24 hr while stirring. The solvent was distilled off under reduced pressure to give a crude product. GC analysis of the reactant confirmed that 3-chloro-1-phenylpropane-1-ol with optical purity of 90percent ee was produced in 9percent yield. Comparison with Example E-1 demonstrated the superiority of the asymmetric reduction using a potassium formate solution as the hydrogen source.

Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 39, p. 5207 - 5210
[2] Synthetic Communications, 2009, vol. 39, # 15, p. 2737 - 2746
[3] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 431 - 435
[4] Chemical Communications, 2015, vol. 51, # 26, p. 5725 - 5727
[5] European Journal of Medicinal Chemistry, 2016, vol. 109, p. 157 - 172
[6] Patent: KR2015/116956, 2015, A, . Location in patent: Paragraph 0143; 0156-0158
[7] Patent: KR2016/44117, 2016, A, . Location in patent: Paragraph 0069-0072
[8] Organic and Biomolecular Chemistry, 2014, vol. 12, # 6, p. 1009 - 1017
[9] Patent: CN105061126, 2017, B, . Location in patent: Paragraph 0095; 0096; 0097; 0098; 0099
[10] Patent: US2008/200672, 2008, A1, . Location in patent: Page/Page column 7
[11] Patent: CN105732309, 2016, A, . Location in patent: Paragraph 0037; 0049; 0050
[12] Chinese Journal of Chemistry, 2013, vol. 31, # 3, p. 349 - 354
[13] Organic Letters, 2016, vol. 18, # 18, p. 4658 - 4661
[14] Patent: US2009/62573, 2009, A1, . Location in patent: Page/Page column 8; 14
[15] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6495 - 6497
[16] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 11, p. 1767 - 1769
[17] Tetrahedron Asymmetry, 1992, vol. 3, # 4, p. 525 - 528
[18] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4929 - 4931
[19] Organic Process Research and Development, 2012, vol. 16, # 4, p. 710 - 713
[20] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1697 - 1702
[21] Chemical Communications, 2015, vol. 51, # 86, p. 15728 - 15731
[22] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2119 - 2124
[23] Angewandte Chemie - International Edition, 2018, vol. 57, # 32, p. 10231 - 10235[24] Angew. Chem., 2018, vol. 130, p. 10388 - 10392,5
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YieldReaction ConditionsOperation in experiment
75% With dimethylsulfide borane complex; C23H22BNO3 In tetrahydrofuran at 20℃; for 2 h; Cat-5 (0.05 mmol, 20 mg) prepared in Preparation Example 2.5 was dissolved in 1 ml of THF, BH3-DMS (0.42 mmol, 0.04 ml) was added, and the mixture was stirred for about 7 minutes. A solution of 3-chloropropiophenone (0.6 mmol, 100 mg) in 0.45 ml of THF was added dropwise to the reaction mixture. After reacting at room temperature for 2 hours, the reaction was terminated by the addition of methanol. (R) -3-chloro-1-phenylpropanol (yield: 75percent, 73percent ee) was obtained in the same manner as in Example 1.1.
77 % ee With hydrogen In methanol at 60℃; for 24 h; 6.127 mg (8.0 μmol) of Cp*Ir(OTf)[(S,S)-MsDPEN] and 1.249 g (8.0 mmol) of β-chloropropiophenone were introduced in an autoclave, and the mixture was subjected to argon substitution. 3.3 mL of methanol was introduced and deaeration was performed, then hydrogen gas was introduced at 10 atm and the resulting mixture was maintained at 60° C. for 24 hr while stirring. The solvent was distilled off under reduced pressure to give a crude product. GC analysis of the reactant confirmed that 3-chloro-1-phenylpropane-1-ol with optical purity of 77percent ee was produced in 12percent yield. Comparison with Example E-1 demonstrated the superiority of the asymmetric reduction using a potassium formate solution as the hydrogen source.
80 % ee With dimethylsulfide borane complex; (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine In tetrahydrofuran at 20℃; for 1 h; General procedure: To a solution of 1 (0.005–0.01 mmol, 0.5–1 mol percent) in dry THF(3 mL) at room temperature, a solution of BH3SMe2 (10 M,100 lL, 1 mmol) in THF (2 mL) was added dropwise at a rate of3.2 mL per hour using a syringe pump. At the same time a solutionof ketone (1 mmol) in THF (2 mL) was also added to the reactionflask at a rate of 3 mL per hour. After the addition of both reagents,the reaction mixture was stirred for 20 min, quenched by the additionof MeOH (1 mL) at room temperature, and stirred for 30 min. Subsequently, the solvents were evaporated under vacuum and theproduct was isolated by column chromatography using hexane/EtOAc (4:1) as the eluent.
66 % ee at 20℃; for 20 h; General procedure: A flask was charged with azolium salt L12 (0.02 mmol, 9.1 mg),Ag2O (0.01 mmol, 2.4 mg) and CH2Cl2(1 mL). After stirring the resulting mixture at room temperature for 2 h in the dark, CH2Cl2 was removed in vacuo. Then, a THF (1 mL) solution of [IrCl(cod)]2(0.01 mmol, 6.9 mg) was added to the reaction vessel. The resulting mixture was stirred at room temperature for an additional 4 h in the dark, filtered through a membrane filter, and evaporated to dry-ness in vacuo. Subsequently, to the resulting flask containing yellow solid of the unpurified IrCl(cod)(NHC) complex, a solution of AgBF4(0.025 mmol, 4.9 mg) in CPME (2 mL) was added, and then stirred at room temperature for 1 h. Finally, propiophenone (0.5 mmol,66 mg) and (EtO)2MeSiH (2.25 mmol, 294 mg) were added to the resulting CPME solution (see Appendix A. Supplementary data fordetails). After stirring at room temperature for 20 h under open-air conditions, K2CO3(2 mg) and MeOH (2 mL) were added. Then, the resulting mixture was stirred at room temperature for 2 h. Afterevaporation of the solvents, the residue obtained was purified bycolumn chromatography on silica gel (Et2O/n-hexane = 3:7) to give(S)-1-phenyl-1-propanol (61 mg, 91percent isolated yield). The ee was measured by chiral GLC.

Reference: [1] Patent: KR2015/116956, 2015, A, . Location in patent: Paragraph 0143; 0154; 0155
[2] Tetrahedron Letters, 2005, vol. 46, # 3, p. 495 - 498
[3] Tetrahedron Letters, 1993, vol. 34, # 26, p. 4145 - 4148
[4] Journal of the Chemical Society, Chemical Communications, 1986, # 13, p. 1018 - 1019
[5] Tetrahedron, 2002, vol. 58, # 6, p. 1069 - 1074
[6] Tetrahedron Asymmetry, 2001, vol. 12, # 16, p. 2323 - 2329
[7] Organic Letters, 2006, vol. 8, # 14, p. 2969 - 2972
[8] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5799 - 5802
[9] Patent: US2009/62573, 2009, A1, . Location in patent: Page/Page column 8; 14
[10] Organic Letters, 2009, vol. 11, # 2, p. 305 - 308
[11] Organic Process Research and Development, 2012, vol. 16, # 4, p. 710 - 713
[12] Green Chemistry, 2014, vol. 16, # 5, p. 2680 - 2688
[13] Catalysis Letters, 2014, vol. 144, # 7, p. 1289 - 1295
[14] Chemistry - A European Journal, 2014, vol. 20, # 38, p. 12190 - 12200
[15] Tetrahedron Asymmetry, 2015, vol. 26, # 24, p. 1453 - 1458
[16] Organic and Biomolecular Chemistry, 2016, vol. 14, # 18, p. 4304 - 4311
[17] Journal of Molecular Catalysis A: Chemical, 2016, vol. 421, p. 138 - 145
[18] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 426 - 431
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YieldReaction ConditionsOperation in experiment
60.526 % ee at 28℃; for 48 h; Microbiological reaction; Enzymatic reaction General procedure: Fresh plates of each yeast strain were streaked from the frozen stock in PDA. A single colony was used to inoculate 100mL of YM Broth. The culture was incubated at 28°C and 150rpm for 48h and the cells were collected by centrifugation at 4000rpm and 4°C for 15min. The pellet was washed three times with 50mL physiological serum. Afterward, 2g of yeast cells (wet weight) were suspended in 20mL of 10percent dextrose solution and 30mg of the appropriate substrate were added. The culture was incubated at 28°C and 150rpm in an orbital shaker ZHICHENG ZHWY-211B for 48h.
23 %Chromat. With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 6 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 94 - 98
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
21 %Chromat. With yeast culture of Aphanocladium album KCh 417 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33 %Chromat. With yeast culture of Saccharomyces cerevisiae KCh 464 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
33 %Chromat. With yeast culture of Saccharomyces pastorianus KCh 906 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[3] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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  • [ 100306-34-1 ]
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  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
33 %Chromat. With yeast culture of Candida parapsilosis KCh 909 In acetone at 25℃; for 72 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
57 %Chromat. With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 144 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
[2] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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  • [ 100306-33-0 ]
  • [ 93-55-0 ]
YieldReaction ConditionsOperation in experiment
61 %Chromat. With yeast culture of Saccharomyces brasiliensis KCh 905 In acetone at 25℃; for 24 h; Microbiological reaction General procedure: Erlenmeyer flasks (300 ml), each containing 100 ml of the mediumconsisting of 3 g glucose and 1 g aminobac dissolved in water,were inoculated with a suspension of microorganisms and then incubated for 3–7 days at 25 C on a rotary shaker (190 rpm). After full growth of the culture 20 mg of a substrate dissolved in 1 ml of acetone was added. After 1, 3, 6, 9, 12 h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 5 ml of the transformation mixture were taken out and extracted with CHCl3(3*10 ml). The extracts were dried over MgSO4, concentrated in vacuo, and analyzed by GC. All the experiments were repeatedthree times.
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 18-19, p. 1264 - 1269
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Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 19, p. 6495 - 6497
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Reference: [1] Tetrahedron Asymmetry, 2001, vol. 12, # 7, p. 1025 - 1034
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Reference: [1] Science, 2016, vol. 352, # 6281, p. 61 - 67
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