3-Chloro-1-phenyl-1-propanol

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: 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.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.30In 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 16.5gGeneral procedure: To a solution of 4-benzoyloxy-1-phenylbutyl nitrate 2a (52.5 mg, 0.166 mmol) in EtOH (1.7 mL) was added 2 mL of 44percent aqueous ammonium sulfide solution at room temperature. The reaction mixture was stirred for 1 h, then the reaction was quenched with H2O. The mixture was extracted with Et2O (.x.3), washed with brine, dried over Na2SO4, and concentrated. The residue was purified with flash column chromatography (silica gel, hexane-EtOAc 10:1 to 5:1) to provide 4-hydroxy-4-phenylbutyl benzoate 5a in 100percent yield (45 mg).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 CHCl

An intermediate of racemic Atomoxetine.

Molecular Weight:170.63
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:170.0498427
Monoisotopic Mass:170.0498427
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:99.7
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes