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Chemistry
Organic Building Blocks
Epoxides
2-(phenoxymethyl)oxirane
(S)-Glycidyl phenyl ether
Chemistry
Organic Building Blocks
Heterocyclic Building Blocks Asymmetric Synthesis
Epoxides
Aryls Ethers Chiral Building Blocks Benzene Compounds
2-(phenoxymethyl)oxirane

[ CAS No. 71031-03-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Quality Control of [ 71031-03-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 71031-03-3 ]

Product Details of [ 71031-03-3 ]

CAS No. :71031-03-3 MDL No. :MFCD06659026
Formula : C9H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FQYUMYWMJTYZTK-SECBINFHSA-N
M.W : 150.17 Pubchem ID :1534345
Synonyms :

Calculated chemistry of [ 71031-03-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.68
TPSA : 21.76 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 2.57
Consensus Log Po/w : 1.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.89
Solubility : 1.92 mg/ml ; 0.0128 mol/l
Class : Very soluble
Log S (Ali) : -1.41
Solubility : 5.86 mg/ml ; 0.039 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.407 mg/ml ; 0.00271 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 71031-03-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P201-P261-P273-P280-P305+P351+P338-P308+P313 UN#:1760
Hazard Statements:H227-H312+H332-H315-H317-H318-H335-H350-H412 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 71031-03-3 ]

* 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.

  • Downstream synthetic route of [ 71031-03-3 ]

[ 71031-03-3 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 1746-13-0 ]
  • [ 71031-03-3 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With oxygen at 30℃; for 12h; P1 medium for bacteria growth; Title compound not separated from byproducts;
46 % ee With whole E. coli cells expressing monooxygenase from Herbaspirillum huttiense HhMO and NADH-dependent flavin oxidoreductase PsStyB In aq. phosphate buffer; octane at 37℃; Green chemistry; Enzymatic reaction; Overall yield = 11 percent; enantioselective reaction;
Reference： [1]Fu, Hong; Shen, Gwo-Jenn; Wong, Chi-Huey [Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 167 - 170]
[2]Lin, Hui; Tang, Yanhong; Dong, Shuang; Lang, Ruibo; Chen, Hongge [Catalysis science and technology, 2020, vol. 10, # 7, p. 2145 - 2151]
  • 2
  • [ 71031-03-3 ]
  • [ 112243-65-9 ]
YieldReaction ConditionsOperation in experiment
With ammonia In ethanol at 50℃;
Multi-step reaction with 2 steps 1: methanol 2: HCO2NH4 / Pd/C
3 (2S)-1-Amino-3-phenoxypropan-2-ol EXAMPLE 3 (2S)-1-Amino-3-phenoxypropan-2-ol The title compound was prepared from (2S)-2-phenoxymethyl-oxirane (which was obtained in Example 2) according to the procedure of Example 1 with one change. The free base was obtained as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.56 (dd, J=12.8, 6.3 Hz, 1H), 2.67 (dd, J=12.8, 4.9 Hz, 1H), 3.65-3.75 (m, 1H), 3.82 (dd, J=9.8, 6.0 Hz, 1H), 3.93 (dd, J=9.8, 5.0 Hz, 1H), 6.85-6.95 (m, 3H), 7.20-7.30 (m, 2H); MS (ES) m/z: 167.7 (MH+); HRMS Calcd. for C9H13NO2 (M+): 167.0946. Found: 167.0945.
Reference： [1]Ader, Ulrich; Schneider, Manfred P. [Tetrahedron Asymmetry, 1992, vol. 3, # 2, p. 205 - 208]
[2]Hu, Baihua; Ellingboe, John; Gunawan, Iwan; Han, Stella; Largis, Elwood; Li, Zenan; Malamas, Michael; Mulvey, Ruth; Oliphant, Alexander; Sum, Fuk-Wah; Tillett, Jeff; Wong, Victoria [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 6, p. 757 - 760]
[3]Current Patent Assignee: PFIZER INC
  • 3
  • [ 140630-45-1 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; isopropyl alcohol; at 0 - 20℃; for 1h; Example 4 Preparation of (S)-glycidylphenyl ether To a mixture of N',N'-disalicylidene ethylenediaminatocobalt(II) (173 mg, 0.532 mmol) and dichloromethane (13 ml) was added (+-) camphorsulfonic acid (148 mg, 0.638 mmol) and the reaction system was stirred for 1 hour while being filled with air.The reaction solution was evaporated to dryness under reduced pressure to give a crude blackish (dark) brown cobalt (III) complex.Thereto was added tert-butylmethyl ether (5 ml) to disperse the crude cobalt (III) complex and then thereto were added (R)-epichlorohydrin (2.50 ml, 31.9 mmol, optical purity 99% e.e.) and phenol (2.50 g, 26.6 mmol) in order.The mixture was stirred for 24 hours under nitrogen atmosphere at room temperature.After the reaction, the reaction mixture was diluted with tert-butylmethyl ether (20 ml), the solution was washed with a 6% aqueous sodium hydroxide solution (10 ml) and a saturated sodium chloride solution (10 ml) in order, and the organic layer was condensed under reduced pressure to give crude (R)-1-chloro-3-phenoxy-2-propanol (5.44 g).This crude compound (5.44 g) was dissolved in isopropanol (10 ml) and thereto was added a 24% aqueous sodium hydroxide solution (6.64 g, 39.8 mmol) under ice-cooling.The mixture was stirred for 1 hour at room temperature.After the reaction, the reaction mixture was diluted with tert-butylmethyl ether (50 ml) and the solution was washed with water (2.0 ml), a saturated aqueous ammonium solution (20 ml) and a saturated aqueous sodium chloride solution (20 ml) in order.The organic layer was condensed under reduced pressure to give crude (S)-glycidylphenyl ether (3.80 g).Quantitative analysis by gas chromatography and optical purity measurement by HLPC were conducted on the compound.As a result the subject compound, (S)-glycidylphenyl ether (3.71 g, 93.0%) was produced with optical purity at 99% e.e.
Reference： [1]Tetrahedron Asymmetry,1992,vol. 3,p. 205 - 208
[2]Patent: US2004/24254,2004,A1 .Location in patent: Page 5
  • 4
  • [ 115314-14-2 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
95% Synthesis of (S)-2-Phenoxymethyl-oxirane (3a); To a stirred suspension of sodium hydride (60 % dispersion in mineral oil, 126 mg, 3.2 mmol) in Lambda/,Lambda/-dimethylformamide (4 mL) under N2 at 0 0C was added portionwise a solution of phenol (1a, 282 mg, 3.0 mmol) in N, N- dimethylformamide (1 mL) and the reaction mixture was stirred at ambient temperature for 20 min. A solution of (2S)-glycidyl m-nitrobenzenesulfonate (2, 722 mg, 2.78 mmol) in Lambda/,Lambda/-dimethylformamide (2 mL) was then added at 0 0C. The reaction mixture was stirred at ambient temperature for 16 h, poured onto a mixture of ice-water (15 mL) and saturated aqueous ammonium chloride solution (15 mL) and extracted with te/t-butylmethyl ether (3 * 15 mL). The combined organic layers were washed with aqueous 1Lambda/ sodium hydroxide solution (2 * 30 mL), 50 % aqueous saturated brine (2 x 30 mL), and saturated brine (30 ml), dried (Na2SO4) and concentrated under reduced pressure to give (S)-2-phenoxymethyl-oxirane (3a) as a light yellow viscous oil (440 mg, 95 % yield, >95 % pure by LC-MS and 1H-NMR).
Reference： [1]Patent: WO2006/60122,2006,A2 .Location in patent: Page/Page column 26
[2]Tetrahedron,1999,vol. 55,p. 14381 - 14390
[3]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2253 - 2258
[4]Medicinal Chemistry Research,2000,vol. 10,p. 164 - 177
  • 5
  • [ 3202-33-3 ]
  • [ 71031-03-3 ]
  • (R)-1-Phenoxy-3-(4-phenoxy-piperidin-1-yl)-propan-2-ol [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1377 - 1380
  • 6
  • [ 3202-33-3 ]
  • [ 71031-03-3 ]
  • (S)-1-Phenoxy-3-(4-phenoxy-piperidin-1-yl)-propan-2-ol [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1377 - 1380
  • 7
  • [ 113826-06-5 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
73% Preparation 2; Preparation of (25)-2-(phenoxymethYl . oxirane; A solution of phenol (17.57 g, 76.97 mmol) in dry DMF (200 mL) was added slowly to a suspension of sodium hydride (60% in mineral oil, 4.0 g, 100.06 mmol) in DMF at 0C and stirred at the same temperature for 30 minutes. Then, (2S)- (+)-glycidyl tosylate (17.57 g, 76.97 mmol) was added slowly. The resulting mixture was stirred at room temperature overnight and quenched with saturated ammonium chloride solution. The two-phase mixture was diluted with water and extracted with diethyl ether. The combined organic extracts were washed with saturated NaHCO3, brine, dried over anhydrous sodium sulfate, concentrated and purified by medium pressure column chromatography (eluant: hexanes/EtOAc 13: 1). The product was obtained as a colorless oil in 73% yield.
Reference： [1]Tetrahedron Asymmetry,2000,vol. 11,p. 2885 - 2898
[2]Patent: WO2005/56544,2005,A1 .Location in patent: Page/Page column 36
[3]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1377 - 1380
  • 8
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With water;[(1-RR)-(Dibenzoyl-LTA)]; at 5 - 20℃;Resolution of racemate;Product distribution / selectivity; 0.5 mole of racemic 1,2-epoxy compounds were added with 0.4 mole % of the catalyst prepared in Preparation Example 1 [(1-RR)-(Dibenzoyl-LTA) ] (or Preparation Example 2 [ (1-SS) - (Dibenzoyl- DTA)]) and cooled down to 5 G Then 5.4 g of water was slowly added here and stirred at 20 C After fractional distillation under reduced pressure, the target compounds were obtained with more than 99%ee optical purity
Reference： [1]Helvetica Chimica Acta,2008,vol. 91,p. 317 - 332
[2]Heterocycles,1998,vol. 48,p. 1471 - 1476
[3]Patent: WO2008/153280,2008,A1 .Location in patent: Page/Page column 39
[4]Molecular catalysis,2019,vol. 476
  • 9
  • [ 140630-35-9 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In diethyl ether Yield given;
Reference： [1]Annis, D. Allen; Jacobsen, Eric N. [Journal of the American Chemical Society, 1999, vol. 121, # 17, p. 4147 - 4154]
  • 10
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With trimethylsilylazide; β‐cyclodextrin In ethanol; water at 37℃; for 5h; Title compound not separated from byproducts;
With Cu metal organic framework based on (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl*silica packed stainless steel column (10 cm long × 4.0 mm i.d.) In ethanol; hexane at 25℃; Resolution of racemate;
67 % ee With phthalic anhydride; C64H74Al2Cl2N4O4; bis(triphenylphosphine)iminium chloride In toluene at 0℃; for 6h; Inert atmosphere; Resolution of racemate; enantioselective reaction;
75 % ee With phthalic anhydride; C64H74Al2Cl2N4O4; bis(triphenylphosphine)iminium chloride In toluene at 0℃; for 6h; Inert atmosphere; Resolution of racemate; enantioselective reaction;

Reference： [1]Kamal, Ahmed; Arifuddin; Rao, Maddamsetty V. [Tetrahedron Asymmetry, 1999, vol. 10, # 22, p. 4261 - 4264]
[2]Tanaka, Koichi; Kawakita, Tomohiro; Morawiak, Maja; Urbanczyk-Lipkowska, Zofia [CrystEngComm, 2019, vol. 21, # 3, p. 487 - 493]
[3]Li, Jie; Ren, Bai-Hao; Wan, Zhao-Qian; Chen, Shi-Yu; Liu, Ye; Ren, Wei-Min; Lu, Xiao-Bing [Journal of the American Chemical Society, 2019, vol. 141, # 22, p. 8937 - 8942]
[4]Li, Jie; Ren, Bai-Hao; Wan, Zhao-Qian; Chen, Shi-Yu; Liu, Ye; Ren, Wei-Min; Lu, Xiao-Bing [Journal of the American Chemical Society, 2019, vol. 141, # 22, p. 8937 - 8942]
  • 11
  • [ 113826-06-5 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
  • [ 71031-03-3 ]
Reference： [1]Tetrahedron,1999,vol. 55,p. 14381 - 14390
  • 12
  • [ 67843-74-7 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydroxide; benzyltrimethylammonium chloride; In water; toluene; at 0 - 20℃; for 40.5h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 30.0g, 0.32mol), benzyltrimethylammonium chloride (0.80g), toluene (70ml) and water (70ml), and the mixture was cooled with ice. After addition of phenol (20.3g, 0.22mol), thereto 24% aqueous NaOH solution (54.0g, 0.33mol) was dropped in a period of one hour under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 39 hours at room temperature. After the reaction the aqueous layer was removed and the organic layer was neutralized with 5% aqueous HCl solution (70ml) and washed with water (40ml). After removal of toluene, the residue was distilled to give objective (R)-glycidylphenyl ether (27.0g, yield 83%, optical purity 98% ee) as a colorless liquid. bp 85-86C/0.8 Torr NMR (270MHz, CDCl3) ? 2.76 (1H, dd), 2.91 (1H, dd), 3.36 (1H, dddd), 3.97 (1H, dd), 4.21 (1H, dd), 6.91 - 6.99 (3H, m), 7.25 - 7.32 (2H, m)
80% With sodium hydroxide; benzyltrimethylammonium chloride; In water; 1,2-dichloro-ethane; at 0 - 20℃; for 42.67h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64g, 29mmol), benzyltrimethylammonium chloride (36mg), 1,2-dichloroethane (6ml) and water (6ml), and the mixture was cooled with ice. After addition of phenol (1.78g, 19mmol), thereto 24% aqueous NaOH solution (4.10g, 25mmol) was dropped in a ten minute period under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 42 hours at room temperature. After the aqueous layer was removed, the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (2.27g, yield 80%, optical purity 98% ee) as an oil.
75% With sodium hydroxide; benzyltrimethylammonium chloride; In tert-butyl methyl ether; water; at 0 - 20℃; for 37.67h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64g, 29mmol), benzyltrimethylammonium chloride (72mg), tert-butylmethyl ether (6ml) and water (6ml), and the mixture was cooled with ice. After addition of phenol (1.78g, 19mmol), thereto 24% aqueous NaOH solution (4.75g, 29mmol) was dropped in a ten minute period under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 37 hours at room temperature. After the aqueous layer was removed, the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (2.13g, yield 75%, optical purity 98% ee) as an oil.
69% With sodium hydroxide; In water; toluene; at 0 - 20℃; for 50.67h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64g, 29mmol), toluene (6ml) and water (6ml), and the mixture was cooled with ice. After adding phenol (1.78g, 19mmol), thereto 24% aqueous NaOH solution (4.75g, 29mmol) was dropped under stirring over a ten minute period. The mixture was stirred for 30 minutes under ice-cooling and then for 50 hours at room temperature. The aqueous layer was removed and the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (1.96g, yield 69%, optical purity 98% ee) as an oil.
52% With sodium hydroxide; benzyltrimethylammonium chloride; In methanol; water; at 0 - 20℃; for 37.67h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64g, 29mmol), methanol (9ml) and water (6ml), and the mixture was cooled with ice. After phenol (1.79g, 19mmol) was added, thereto 24% aqueous NaOH solution (4.10g, 25mmol) was dropped in a 10 minute period under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 37 hours at room temperature. After removal of methanol, the reaction mixture was extracted with toluene (3.6ml). The organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give crude (R)-glycidyphenyl ether (1.49g, yield 52%, optical purity 92% ee) as an oil.
38% With sodium hydroxide; benzyltrimethylammonium chloride; In tetrahydrofuran; water; at 0 - 20℃; for 41.67h; To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64g, 29mmol), tetrahydrofuran (9ml), benzyltrimethylammonium chloride (36mg) and water (6ml), and the mixture was cooled with ice. After phenol (1.79g, 19mmol) was added, thereto 24% aqueous NaOH solution (4.75g, 29mmol) was dropped in a 10 minute period under stirring. The mixture was stirred for 30 minute under ice-cooling and then for 41 hours at room temperature. After removal of tetrahydrofuran, the reaction mixture was extracted with toluene. The organic layer was neutralized 5% HCl and washed with water twice. The solvent was removed to give crude (R)-glycidyphenyl ether (1.08g, yield 38%, optical purity 92% ee) as an oil.

Reference： [1]Patent: EP1508568,2005,A1 .Location in patent: Page 4
[2]Patent: EP1508568,2005,A1 .Location in patent: Page 5
[3]Patent: EP1508568,2005,A1 .Location in patent: Page 5
[4]Patent: EP1508568,2005,A1 .Location in patent: Page 5
[5]Patent: EP1508568,2005,A1 .Location in patent: Page 6
[6]Patent: EP1508568,2005,A1 .Location in patent: Page 6
[7]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 3243 - 3248
  • 13
  • [ 71031-03-3 ]
  • [ 103-49-1 ]
  • [ 437764-00-6 ]
YieldReaction ConditionsOperation in experiment
99% In methanol;Heating / reflux; Preparation 3; Preparation of (2-l- (dibenzylamino)-3-phenoxy-2-propanol; A reaction mixture containing (2S)-2- (phenoxymethyl) oxirane (Preparation 2,8. 44 g, 65.20 mmol) and dibenzylamine (12.20 g, 61.82 mmol, 1.1 eq. ) in MeOH (300 mL) was heated at reflux over- night. The resulting solution was concentrated in vacuo and the crude product was purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, eluant: hexanes/EtOAc 10: 1). The product was obtained as a colorless oil in 99% yield. LC-MS, Method 1: M+H+ = 348.3, retention time = 2.22 min; Rf= 0.42 (hexanes/EtOAc 6: 1).
Reference： [1]Patent: WO2005/56544,2005,A1 .Location in patent: Page/Page column 36
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 757 - 760
  • 14
  • [ 64024-63-1 ]
  • [ 71031-03-3 ]
  • [ 415902-43-1 ]
Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 2456 - 2457
  • 15
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
  • [ 71031-03-3 ]
  • (S)-3-phenoxy-1,2-propanediol [ No CAS ]
  • [ 82430-38-4 ]
YieldReaction ConditionsOperation in experiment
With water In tetrahydrofuran Title compound not separated from byproducts;
With LW202 epoxide hydrolase; water
With Aspergillus niger epoxide hydrolase LW202 mutant Title compound not separated from byproducts;
In tetrahydrofuran; water at 0℃; for 12h; Title compound not separated from byproducts.;
In tetrahydrofuran; water at 0℃; for 12h; Title compound not separated from byproducts.;
With water at 24.84℃; for 48h; Title compound not separated from byproducts.;
With epoxide hydrolase from Aspergillus niger In acetonitrile at 30℃; for 1h; aq. phosphate buffer; Enzymatic reaction;
1: 85 % ee 2: 85 % ee With C65H56CoN3O8; water In dichloromethane enantioselective reaction;
1: 86 % ee 2: 86 % ee With C65H56CoN3O8; water In dichloromethane enantioselective reaction;

Reference： [1]Bredikhin; Strunskaya; Novikova; Azancheev; Sharafutdinova; Bredikhina [Russian Chemical Bulletin, 2004, vol. 53, # 1, p. 213 - 218]
[2]Belder, Detlev; Ludwig, Martin; Wang, Li-Wen; Reetz, Manfred T. [Angewandte Chemie - International Edition, 2006, vol. 45, # 15, p. 2463 - 2466]
[3]Reetz, Manfred T.; Wang, Li-Wen; Bocola, Marco [Angewandte Chemie - International Edition, 2006, vol. 45, # 8, p. 1236 - 1241]
[4]Dey, Sangeeta; Powell, Douglas R.; Hu, Chunhua; Berkowitz, David B. [Angewandte Chemie - International Edition, 2007, vol. 46, # 37, p. 7010 - 7014]
[5]Dey, Sangeeta; Powell, Douglas R.; Hu, Chunhua; Berkowitz, David B. [Angewandte Chemie - International Edition, 2007, vol. 46, # 37, p. 7010 - 7014]
[6]Yang, Heng Quan; Zhang, Lei; Zhong, Lin; Yang, Qi Hua; Li, Can [Angewandte Chemie - International Edition, 2007, vol. 46, # 36, p. 6861 - 6865]
[7]Location in patent: experimental part Feng, Xiaojiang; Sanchis, Joaquin; Reetz, Manfred T.; Rabitz, Herschel [Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5646 - 5654]
[8]Tak, Rajkumar; Kumar, Manish; Menapara, Tusharkumar; Gupta, Naveen; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Suresh [Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3990 - 4001]
[9]Tak, Rajkumar; Kumar, Manish; Menapara, Tusharkumar; Gupta, Naveen; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Suresh [Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3990 - 4001]
  • 16
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
  • [ 538-43-2 ]
  • [ 82430-38-4 ]
Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8058 - 8061
[2]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315
[3]Synthetic Communications,2006,vol. 36,p. 2371 - 2383
[4]Kinetics and Catalysis,2011,vol. 52,p. 691 - 696
[5]Synthetic Communications,2008,vol. 38,p. 1236 - 1248
[6]Synthesis,2007,p. 583 - 589
[7]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315
[8]Angewandte Chemie - International Edition,2006,vol. 45,p. 1309 - 1312
[9]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 63,p. 128 - 134
[10]ChemCatChem,2018,vol. 10,p. 4761 - 4767
  • 17
  • [ 13472-00-9 ]
  • [ 71031-03-3 ]
  • [ 159183-35-4 ]
YieldReaction ConditionsOperation in experiment
46% In tetrahydrofuran; Step b) (2 S)-1-[(4-Aminophenethyl)amino]-3-phenoxy-2-propanol This compound was prepared from (2 S)-2-(phenoxymethyl)oxirane and 4-(2-aminoethyl)aniline as described in example 1, step b, with one modification, the mixture was stirred at 70 C. in tetrahydrofuran. The solvent was removed in vacuo and the product was triturated with ethyl ether to give a white solid (46% yield): MS m/e 286 M+, 1H NMR (CDCI3 300 MHz) delta1.54 (br 1 H), 2.70 (m, 3 H), 2.85 (m, 3 H), 3.40 (br, 1 H), 3.57 (s, 2 H), 3.96 (m, 2 H), 4.01 (m, 1 H), 6.64 (d, 2 H), 6.88 (d, 2 H), 6.90 (m, 3 H), 7.25 (m, 2 H); Analysis for C17H22N2O2 Calc'd: C, 71.30; H, 7.74; N, 9.78 Found: C, 70.83; H, 7.72; N, 9.83.
Reference： [1]Patent: US2002/32222,2002,A1
[2]Medicinal Chemistry Research,2000,vol. 10,p. 164 - 177
  • 18
  • [ 4248-19-5 ]
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
  • (S)-2-phenoxymethylaziridine-1-carboxylic acid tert-butyl ester [ No CAS ]
Reference： [1]Organic Letters,2004,vol. 6,p. 3973 - 3975
  • 19
  • [ 122-60-1 ]
  • [ 84418-43-9 ]
  • [ 71031-03-3 ]
  • ((S)-2-hydroxy-3-phenoxypropyl)carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]
Reference： [1]Organic Letters,2004,vol. 6,p. 3973 - 3975
  • 20
  • [ 122-60-1 ]
  • [ 71031-03-3 ]
  • [ 82430-38-4 ]
Reference： [1]RSC Advances,2018,vol. 8,p. 12918 - 12926
[2]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3990 - 4001
[3]Journal of the American Chemical Society,2002,vol. 124,p. 1307 - 1315
[4]Tetrahedron Asymmetry,2010,vol. 21,p. 2825 - 2829
[5]Journal of the American Chemical Society,2007,vol. 129,p. 1105 - 1112
[6]Catalysis science and technology,2014,vol. 4,p. 3899 - 3908
[7]Kinetics and Catalysis,2011,vol. 52,p. 691 - 696
[8]Helvetica Chimica Acta,2008,vol. 91,p. 317 - 332
[9]Journal of the American Chemical Society,2011,vol. 133,p. 14260 - 14263
  • 21
  • [ 106-89-8 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
  • [ 140630-45-1 ]
Reference： [1]Synthesis,2007,p. 583 - 589
  • 22
  • (R)-2-bromo-3-phenoxypropanol [ No CAS ]
  • [ 71031-03-3 ]
Reference： [1]European Journal of Organic Chemistry,2007,p. 1091 - 1100
  • 23
  • [ 3132-64-7 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 24
  • [ 106-41-2 ]
  • [ 71031-03-3 ]
  • C15H15O3Br [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 25
  • [ 402-45-9 ]
  • [ 71031-03-3 ]
  • (R)-1-phenoxy-3-[4-(trifluoromethyl)phenoxy]propan-2-ol [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 26
  • [ 71031-03-3 ]
  • [ 99-93-4 ]
  • C17H18O4 [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 27
  • [ 371-41-5 ]
  • [ 71031-03-3 ]
  • C15H15O3F [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 28
  • [ 367-12-4 ]
  • [ 71031-03-3 ]
  • C15H15O3F [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 29
  • [ 95-57-8 ]
  • [ 71031-03-3 ]
  • (R)-1-(2-chlorophenoxy)-3-phenoxypropan-2-ol [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 30
  • [ 71031-03-3 ]
  • [ 108-39-4 ]
  • C16H18O3 [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 31
  • [ 767-00-0 ]
  • [ 71031-03-3 ]
  • C16H15O3N [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 32
  • [ 100-02-7 ]
  • [ 71031-03-3 ]
  • C15H15O5N [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 33
  • [ 828-27-3 ]
  • [ 71031-03-3 ]
  • C16H15O4F3 [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 1245 - 1248
  • 34
  • [ 31252-42-3 ]
  • [ 71031-03-3 ]
  • 1-(4-Benzyl-piperidin-1-yl)-3-phenoxy-propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ytterbium(III) triflate In dichloromethane at 25℃; for 16h;
Reference： [1]Peukert, Stefan; Jacobsen, Eric N. [Organic Letters, 1999, vol. 1, # 8, p. 1245 - 1248]
  • 35
  • [ 92-54-6 ]
  • [ 71031-03-3 ]
  • C19H24O2N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81 % Spectr. With ytterbium(III) triflate In dichloromethane at 25℃; for 16h;
Reference： [1]Peukert, Stefan; Jacobsen, Eric N. [Organic Letters, 1999, vol. 1, # 8, p. 1245 - 1248]
  • 36
  • [ 71031-03-3 ]
  • [ 100-61-8 ]
  • C16H19O2N [ No CAS ]
YieldReaction ConditionsOperation in experiment
87 % Spectr. With copper(II) bis(trifluoromethanesulfonate) In diethyl ether at 25℃; for 16h;
Reference： [1]Peukert, Stefan; Jacobsen, Eric N. [Organic Letters, 1999, vol. 1, # 8, p. 1245 - 1248]
  • 37
  • [ 110-91-8 ]
  • [ 71031-03-3 ]
  • (S)-1-morpholino-3-phenoxypropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85 % Spectr. With ytterbium(III) triflate In dichloromethane at 25℃; for 16h;
Reference： [1]Peukert, Stefan; Jacobsen, Eric N. [Organic Letters, 1999, vol. 1, # 8, p. 1245 - 1248]
  • 38
  • [ 71031-03-3 ]
  • [ 109-89-7 ]
  • [ 15288-08-1 ]
YieldReaction ConditionsOperation in experiment
With ytterbium(III) triflate In dichloromethane at 25℃; for 16h;
Reference： [1]Peukert, Stefan; Jacobsen, Eric N. [Organic Letters, 1999, vol. 1, # 8, p. 1245 - 1248]
  • 39
  • [ 940-47-6 ]
  • [ 71031-03-3 ]
  • [ 140630-45-1 ]
YieldReaction ConditionsOperation in experiment
1: 55 % Chromat. 2: 45 % Chromat. With isopropyl alcohol In various solvent(s) at 30℃; for 5h;
1: 93 %Chromat. 2: 7 %Chromat. With Agrobacterium radiobacter AD1 halohydrin dehalogenase HheC; isopropyl alcohol at 30℃; for 24h; aq. buffer; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;
Reference： [1]Seisser, Birgit; Lavandera, Ivan; Faber, Kurt; Spelberg, Jeffrey H. Lutje; Kroutil, Wolfgang [Advanced Synthesis and Catalysis, 2007, vol. 349, # 8-9, p. 1399 - 1404]
[2]Location in patent: experimental part Schrittwieser, Joerg H.; Lavandera, Ivan; Seisser, Birgit; Mautner, Barbara; Lutje Spelberg, Jeffrey H.; Kroutil, Wolfgang [Tetrahedron Asymmetry, 2009, vol. 20, # 4, p. 483 - 488]
  • 40
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (CF3)3COH, polystyrene-bound (R,R)-N-(3,5-di-t-butyl-6-hydroxy)benzylidene-N'-(3-t-butyl-2,5-dihydroxy)benzylidene-1,2-cyclohexanediamine / 2 h / Ambient temperature 2: KOH / diethyl ether
Reference： [1]Annis, D. Allen; Jacobsen, Eric N. [Journal of the American Chemical Society, 1999, vol. 121, # 17, p. 4147 - 4154]
  • 41
  • [ 71031-03-3 ]
  • [ 129689-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.61 g / propan-2-ol / 16 h / Heating 2: H2, acetic acid / 10percent Pd/C / methanol / 48 h / 60 °C / 15001.2 Torr
Reference： [1]Howe; Rao; Holloway; Stribling [Journal of Medicinal Chemistry, 1992, vol. 35, # 10, p. 1759 - 1764]
  • 42
  • [ 854456-01-2 ]
  • [ 71031-03-3 ]
  • [ 854456-05-6 ]
YieldReaction ConditionsOperation in experiment
55% In acetonitrile; for 120h;Heating / reflux; Preparation 13; Preparation of (2S)-1-(benzyl[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}amino)-3-phen- oxYpropan-2-ol; A solution of N-benzyl-1-[(2R)-6-iodo-3, 4-dihydro-2H-chromen-2-yl] methanamine (Preparation 12,8. 28 g, 21.8 mmol) and (22-2-(phenoxymethyl) oxirane (Preparation 2,3. 28 g, 21.8 mmol) in CH3CN (100 mL) was stirred at reflux for 5 days. The volatiles were removed and the residue was purified by silica column chromatography (eluant: hexanes/EtOAc, gradient 9: 1-4: 1) to provide the product (6.4 g, 55%) as a gum.
Reference： [1]Patent: WO2005/56544,2005,A1 .Location in patent: Page/Page column 41
  • 43
  • [ 71031-03-3 ]
  • [ 87120-72-7 ]
  • [ 890017-17-1 ]
YieldReaction ConditionsOperation in experiment
72% In ethanol; at 20 - 90℃; for 4h; Synthesis of 4-((S)-2-hvdroxy-3-phenoxy-propylamino)-piperidine-1 -carboxylic acid terf-butyl ester (5a); To a stirred solution of 2-phenoxymethyl-oxirane (3a, 440 mg, 2.65 mmol) in ethanol (15 mL) at ambient temperature was added 4-amino- piperidine-1 -carboxylic acid terf-butyl ester (4, 1.5 g, 7.49 mmol). The reaction mixture was heated to 90 0C, stirred at this temperature for 4 h and then concentrated under reduced pressure. The light yellow oily residue was purified by flash column chromatography over silica gel eluting with dichloro- methane / methanol (19:1 ). Fractions with Rf = 0.28 (dichloromethane / methanol 9:1 ) were combined and concentrated under reduced pressure to give 4-(2-hydroxy-3-phenoxy-propylamino)-piperidine-1 -carboxylic acid tert-butyl ester (5a) as a colorless, highly viscous oil (757 mg, 72 % yield, 98 % pure by LC-MS and 1H-NMR).
Reference： [1]Patent: WO2006/60122,2006,A2 .Location in patent: Page/Page column 26
  • 44
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 71031-03-3 ]
  • [ 202414-94-6 ]
YieldReaction ConditionsOperation in experiment
90% 4-aminopyridine; dicobalt octacarbonyl; In methanol; at 30℃; under 3750.38 Torr; for 30h; In a 50mL-volumeric autoclave were added deaerated methanol (20mL), 4-aminopyridine (47mg, 0.5 mmol) and (S)-phenylglycidyl ether (3.0g, 20 mmol, >99%ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (0.5MPa) was introduced therein and the mixture was reacted at 30C for 30 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-phenoxy-3-hydroxybutanoic acid methyl ester (3.8g, 90%, >99%ee) as a colorless oil.
Reference： [1]Patent: EP1616852,2006,A1 .Location in patent: Page/Page column 6
  • 45
  • [ 6078-06-4 ]
  • [ 71031-03-3 ]
  • [ 259799-27-4 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 1 Preparation 1 Preparation 1 A mixture of methyl 3-aminobutyrate (4.3 g), (2S)-3-phenoxy-1,2-epoxypropane (4.59 g), ytterbium(III) trifluoromethanesulfonate (1.8 g) and dichloromethane (25 ml) was stirred at 40° C. for 2 hours and at room temperature overnight, worked up in the usual manner and purified by silica gel column chromatography (toluene:ethanol:concentrated ammonia water=9:1:0.1) to give (3RS)-3-[((2S)-2-hydroxy-3-phenoxypropyl)amino]butyric acid methyl ester (2.59 g). IR (Neat): 3400 (br m), 1734 (s), 1599 (m), 1495 (m), 1458 (m), 1298 (m), 1246 (s), 1041 (m), 756 (m) cm-1 NMR (CDCl3, δ): 1.16 (3H, d, J=5.2 Hz), 2.41-2.46 (2H, m), 2.6-3.0 (2H, m), 3.14 (1H, quartet, J=6.4 Hz), 3.68 (3H, s), 3.9-4.1 (3H, m), 6.90-6.99 (3H, m), 7.24-7.33 (2H, m) MS m/z: 268 (M++1)
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2003/181726, 2003, A1
  • 46
  • (2R)-N-Benzyl-4,4-bis(4-methoxyphenyl)-2-butylamine hydrochloride [ No CAS ]
  • [ 7646-78-8 ]
  • [ 71031-03-3 ]
  • (2S)-1-[N-benzyl-[(2R)-4,4-bis(4-methoxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydrogencarbonate; sodium fluoride In dichloromethane; ethyl acetate 2 EXAMPLE 2 EXAMPLE 2 (2R)-N-Benzyl-4,4-bis(4-methoxyphenyl)-2-butylamine hydrochloride (412 mg) was converted to the corresponding free base in a usual manner. 1.0M Solution of tin(IV) chloride in dichloromethane (1.5 ml) was added dropwise to a stirred solution of the free base and (2S)-3-phenoxy-1,2-epoxypropane (225 mg) (IL FARMACO, 50 (10), 643 (1995)) in dichloromethane (4 ml) at -10--5° C. under a nitrogen atmosphere over 10 minutes and the resulting mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was poured into 1N hydrochloric acid and the mixture was stirred under ice cooling for 20 minutes. The organic layer was separated, washed with an aqueous solution of sodium fluoride and a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (ethyl acetate) over silica gel (11 g) and the elude was treated with 4N hydrogen chloride in ethyl acetate to afford (2S)-1-[N-benzyl-[(2R)-4,4-bis(4-methoxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride (136 mg) as an oil. IR (Film): 3292, 2850-2400, 1243 cm-1 NMR (CDCl3, δ): 1.27 and 1.47 (3H, each d, J=6.2 and 6.6 Hz), 2.08 (1H, m), 2.9-3.5 (4H, m), 3.68-4.0 (2H, m), 3.74, 3.75 and 3.76 (6H, each s), 4.02-4.08 (2H, m), 4.10-4.26 (1H, m), 4.3-4.6 (1H, m), 6.72-7.43 and 7.64-7.68 (18H, m) MS m/z 526 (M++1)
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2003/181726, 2003, A1
  • 47
  • [ 101287-11-0 ]
  • [ 71031-03-3 ]
  • (2S)-1-[[(2RS)-4,4-bis(4-hydroxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In diethyl ether; ethanol; ethyl acetate 1 EXAMPLE 1 EXAMPLE 1 A solution of (2S)-3-phenoxy-1,2-epoxypropane (195 mg) (IL FARMACO, 50 (10), 643 (1995)) and 4,4-bis(4-hydroxyphenyl)-2-butylamine (257 mg) in ethanol (2 ml) was stirred under reflux for 24 hours and evaporated in vacuo. The residue was chromatographed (chloroform-methanol) over silica gel (9 g) and the elude was treated with 4N hydrogen chloride in ethyl acetate to afford a crude oil, which was powdered from diethyl ether to afford (2S)-1-[[(2RS)-4,4-bis(4-hydroxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride (117 mg) as a pale brown powder. mp 73° C. (dec.) IR (Nujol): 3600-3100, 2700-2400, 1230 cm-1 NMR (DMSO-d6, δ): 1.21-1.27 (3H, m, CH3), 1.94 (1H, m, CH2), 2.60 (1H, m, CH2), 2.85-3.2 (3H, m, CH2NCH), 3.95 (1H, m, CHAr2), 4.01-4.05 (2H, m, ArOCH2), 4.16 (1H, m, COH), 5.85 (1H, br s, OH), 6.64-6.72 (4H, m, aromatic H), 6.92-7.16 (7H, m, aromatic H), 7.26-7.35 (2H, m, aromatic H), 8.62 (1H, br, NH), 8.92 (1H, br, HCl), 9.23 (1H, br s, OH), 9.28 (1H, br s, OH) MS m/z 408 (M++1)
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2003/181726, 2003, A1
  • 48
  • 3-amino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester acetate [ No CAS ]
  • [ 71031-03-3 ]
  • [ 259798-57-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In methanol 10 EXAMPLE 10 EXAMPLE 10 A mixture of (2S)-3-phenoxy-1,2-epoxypropane (40 mg), 3-amino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester acetate (80 mg), triethylamine (0.5 ml) and methanol (3 ml) was heated under reflux, evaporated and purified by silica gel column chromatography (hexane:ethyl acetate:methanol=1:1:0.07) to give (3RS)-3-((2S)-2-hydroxy-3-phenoxypropyl)-amino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (92 mg). IR (Neat): 2925 (m), 1738 (s), 1597 (m), 1514 (s), 1460 (m), 1263 (m), 1138 (m), 1027 (s), 758 (m) cm-1 NMR (CDCl3, δ): 2.6-2.8 (4H, m), 3.67 (3H, s), 3.87 (6H, s), 3.9-4.0 (2H, m), 4.0-4.1 (2H, m), 6.8-7.0 (7H, m), 7.26 (1H, t, J=8.9 Hz) MS m/z: 390 (M++1)
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2003/181726, 2003, A1
  • 49
  • [ 259799-47-8 ]
  • [ 71031-03-3 ]
  • (2S)-1-phenoxy-3-[[3,3-bis[4-[(methoxycarbonyl)amino]phenyl]propyl]amino]-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;palladium on charcoal; In 1,4-dioxane; methanol; ethanol; EXAMPLE 30 A mixture of (2S)-3-phenoxy-1,2-epoxypropane (0.36 g), N-benzyl-[3,3-bis[4-[(methoxycarbonyl)amino]phenyl]propyl]-amine (0.97 g) and ethanol (10 ml) was heated under reflux for 12 hours and cooled to room temperature. To the reaction mixture, 10% palladium on charcoal (50% wet, 0.4 g), 4N hydrogen chloride in 1,4-dioxane (1.1 ml) and methanol (5 ml) was added. The mixture was stirred under hydrogen (1 atm) for 3.5 hours, filtrated, diluted with ethyl acetate, neutralized by washing with aqueous sodium bicarbonate solution and the organic layer was evaporated. The crude product was purified by silica gel column chromatography(dichloromethane:methanol:concentrated ammonia water=20:1:0.05) to give (2S)-1-phenoxy-3-[[3,3-bis[4-[(methoxycarbonyl)amino]phenyl]propyl]amino]-2-propanol, which was converted to the corresponding hydrochloride salt (0.71 g) in a usual manner. IR (KBr): 3400 (br m), 1711 (s), 1599 (m), 1537 (s), 1317 (m), 1238 (s), 1072 (m), 758 (m) cm-1 NMR (MeOH-d4, delta): 2.3-2.5 (2H, m), 2.9-3.3 (4H, m), 3.65 (3H, s), 3.71 (3H, s), 3.9-4.00 (3H, m), 4.1-4.3 (1H, m), 6.91-6.98 (3H, m), 7.18-7.39 (10H, m) MS m/z: 508 (M++1) (free)
Reference： [1]Patent: US2003/181726,2003,A1
  • 50
  • [ 259872-90-7 ]
  • [ 71031-03-3 ]
  • (2S)-1-[N-benzyl-[(2R)-4,4-bis(4-methoxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In ethanol; ethyl acetate 3 EXAMPLE 3 EXAMPLE 3 (2S)-N-Benzyl-4,4-bis(4-methoxyphenyl)-2-butylamine hydrochloride (412 mg) was converted to the corresponding free base in a usual manner. A solution of the free base and (2S)-3-phenoxy-1,2-epoxypropane (195 mg) (IL FARMACO, 50 (10), 643 (1995)) in ethanol (4 ml) was stirred under reflux for 10 hours, cooled to room temperature, and evaporated in vacuo. The residue was chromatographed (chloroform) over silica gel and the elude was treated with 4N hydrogen chloride in ethyl acetate to afford (2S)-1-[N-benzyl-[(2S)-4,4-bis(4-methoxyphenyl)-2-butyl]amino]-3-phenoxy-2-propanol hydrochloride (549 mg) as an amorphous powder. [α]D24: -22.59° (c=0.54, MeOH) IR (KBr): 3300 (br), 2850-2400, 1248 cm-1 NMR (CDCl3, δ): 1.41 and 1.56 (3H, each d, J=6.6 Hz), 1.64 and 2.05 (1H, m), 2.94-3.6 (4H, m), 3.74, 3.75, 3.76 and 3.77 (6H, each s), 3.87-3.96 (2H, m), 4.05-4.25 (3H, m), 4.5-4.65 and 4.8 (1H, m), 5.9 (1H, br), 6.69-6.98 (8H, m), 7.08-7.17 (4H, m), 7.22-7.41 (4H, m), 7.65-7.73 (2H, m) MS m/z 526 (M++1)
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2003/181726, 2003, A1
  • 51
  • [ 87745-27-5 ]
  • [ 71031-03-3 ]
  • (S)-1-phenoxy-3-[[(S)-1-hydroxy-3-(4-hydroxyphenyl)-2-propyl]amino]-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; EXAMPLE 4 Under nitrogen, a solution of (S)-4-(2-amino-3-hydroxypropyl)phenol hydrochloride (600 mg), (2S)-1,2-epoxy-3-phenoxypropane (308 mg) and N,N-diisopropylethylamine (0.51 ml) in ethanol (10 ml) was refluxed for 3 hours. The mixture was evaporated in vacuo. The residue was chromatographed (chloroform-methanol) over silica gel to afford (S)-1-phenoxy-3-[[(S)-1-hydroxy-3-(4-hydroxyphenyl)-2-propyl]amino]-2-propanol.
Reference： [1]Patent: US2003/73846,2003,A1
  • 52
  • (R,S)-2-amino-3-[3-(3-cyanopyridin-2-yloxy)phenyl]propanol dihydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • [ 7087-68-5 ]
  • (R,S)-3-[3-(3-cyanopyridin-2-yloxy)phenyl]-2-(2-hydroxy-3-phenoxypropyl-amino)propanol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane; ethanol 37 Example 37 Under nitrogen, a solution of (R,S)-2-amino-3-[3-(3-cyanopyridin-2 -yloxy)phenyl]propanol dihydrochloride (415 mg), (2S)-3 -phenoxy-1,2-epoxypropane (192 mg) and N,N-diisopropyl-ethylamine (0.43 ml) in ethanol (10 ml) was refluxed for 7 hours. The mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1), followed by treatment with 4N hydrogen chloride in dioxane to give (R,S)-3-[3-(3 -cyanopyridin-2-yloxy)phenyl]-2-(2-hydroxy-3 -phenoxypropyl-amino)propanol hydrochloride (174.7 mg) as a colorless powder. IR (KBr): 3360-3330, 2227, 1690, 1590, 1425, 1240 cm-1 NMR (DMSO-d6, δ):2.80-3.80 (7H, m), 4.00 (1H, d, J=5.2 Hz), 4.20-4.30 (1H, m), 5.44 (1H, br s), 6.90-7.00 (3H, m), 7.10-7.45 (7H, m), 8.30-8.46 (2H, m), 8.70-8.80 (1H, br s) MS (m/z):420(M+1)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 53
  • [ 71031-03-3 ]
  • [ 152356-05-3 ]
  • (2S)-1-[N-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 1 EXAMPLE 1 EXAMPLE 1 Under nitrogen, to a solution of N-benzyl-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (487 mg) and (2S)-3-phenoxy-1,2,-epoxypropane (338 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (107 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford (2S)-1-[N-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (750 mg). NMR (CHCl3, δ): 1.22-2.15 (4H, m), 2.45-3.10 (6H, m), 3.32-3.39 (1H, m), 3.70-4.10 (7H, m), 4.20-4.25 (1H, m), 6.58-7.00 (7H, m), 7.20-7.45 (6H, m) MASS (m/z): 432 (M+H)+
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2002/120148, 2002, A1
  • 54
  • N-benzyl-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • (2S)-1-[N-benzyl-N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 66 EXAMPLE 66 EXAMPLE 66 under nitrogen, to a solution of N-benzyl-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride (300 mg) and (2S)-1-phenoxy-2,3-epoxypropane (193 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (61 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford (2S)-1-[N-benzyl-N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (340 mg). NMR (CDCl3, δ): 1.20-140 (1H, m), 1.60-2.30 (4H, m), 2.50-2.95 (7H, m), 3.80-4.05 (5H, m), 6.50-6.75 (2H, m), 6.85-7.03 (4H, m), 7.20-7.38 (8H, m) (+) APCI-MASS (m/z): 418 (M+H)+
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2002/120148, 2002, A1
  • 55
  • (2R)-2-amino-3-[4-(3-cyanopyridin-2-yloxy)phenyl]propanol dihydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • (2R)-3-[4-(3-cyanopyridin-2-yloxy)phenyl]-2-((2S)-2-hydroxy-3-phenoxypropylamino)propanol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; methanol 36 Example 36 Example 36 Under nitrogen, a solution of (2R)-2-amino-3-[4-(3 -cyanopyridin-2-yloxy)phenyl]propanol dihydrochloride (4.9 g), (2S)-3-phenoxy-1,2-epoxypropane (5.0 g) and N,N-diisopropylethylamine (4.5 ml) in a mixture of methanol (10 ml) and 1,4-dioxane (10 ml) was refluxed for 28 hours. The mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane:methanol =20:1), followed by treatment with 4N hydrogen chloride in dioxane to give (2R)-3-[4-(3-cyanopyridin-2-yloxy)phenyl]-2 -((2S)-2-hydroxy-3-phenoxypropylamino)propanol hydrochloride (1.5 g). IR (KBr): 3560-3330, 2240, 1648, 1592, 1492 cm-1 NMR (DMSO-d6, δ):2.90-3.00 (1H, m), 3.05-3.80 (6H, m), 4.00 (1H, d, J=5.0 Hz), 4.20-4.30 (1H, m), 5.48 (1H, br s), 5.90 (1H, d, J=5.0 Hz), 6.90-7.05 (3H, m), 7.10-7.50 (7H, m), 8.30-8.45 (2H, m), 8.70-8.80 (1H, br s) MS (m/z):420(M+1)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 56
  • (2S)-2-amino-3-[4-(3-nitropyridin-2-yloxy)phenyl]propanol hydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • [ 282099-39-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; N-ethyl-N,N-diisopropylamine In ethanol; ethyl acetate 38 Example 38 Example 38 Under nitrogen, a solution of (2S)-2-amino-3-[4-(3 -nitropyridin-2-yloxy)phenyl]propanol hydrochloride (3.1 g), (2S)-1,2-epoxy-3-phenoxypropane (1.43 g) and N,N-diisopropylethylamine (3.2 ml) in ethanol (30 ml) was refluxed for 4 hours. The mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=25:1), followed by treatment with 4N hydrogen chloride in ethyl acetate and trituration with ethyl acetate to give (2S)-2-((2S)-2-hydroxy-3 -phenoxypropylamino)-3-[4-(3-nitropyridin-2-yloxy) phenyl]-propanol (0.96 g). MS (m/z):440(M+1)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 57
  • (S)-2-amino-3-[4-(pyrimidin-2-yloxy)phenyl]propan-1-ol dihydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • (2S)-2-((2S)-2-hydroxy-3-phenoxypropylamino)-3-[4-(pyrimidin-2-yloxy)phenyl]propan-1-ol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; ethanol; sodium hydrogencarbonate; ethyl acetate 49 Example 49 Example 49 Under nitrogen, to a solution of (S)-2-amino-3-[4 -(pyrimidin-2-yloxy)phenyl]propan-1-ol dihydrochloride (230 mg) in ethanol (5 ml) were added N,N-diisopropylethylamine (0.62 ml) and (S)-3-phenoxy-1,2-epoxypropane (110 mg) at room temperature, and the mixture was refluxed for 6 hours. After removal of the solvent in vacuo, the residue was dissolved in a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=10:1 to 5:1), followed by treatment with 4N hydrogen chloride in 1,4 -dioxane, trituration with hexane and dryness in vacuo to give (2S)-2-((2S)-2-hydroxy-3-phenoxypropylamino)-3-[4 -(pyrimidin-2-yloxy)phenyl]propan-1-ol dihydrochloride (65 mg). NMR (DMSO-d6, δ):2.85-3.0 (1H, m), 3.1-3.75 (6H, m), 3.9-4.05 (2H, m), 4.2-4.35 (1H, m), 6.9-7.05 (3H, m), 7.1-7.45 (7H, m), 8.64 (2H, d, J=4.8 Hz)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 58
  • (S)-2-amino-3-[4-(quinolin-3-yloxy)phenyl]propan-1-ol dihydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • [ 282099-76-7 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol; ethanol 54 Example 54 Example 54 Under nitrogen, to a stirred solution of (S)-2-amino-3 -[4-(quinolin-3-yloxy)phenyl]propan-1-ol dihydrochloride (200 mg) in ethanol (5 ml) was added sodium methoxide (28% in methanol, 0.21 ml) at 5° C. After 15 minutes, a solution of (S)-3-phenoxy-1,2-epoxypropane (82 mg) in ethanol (1 ml) was added and the mixture was refluxed for 7.5 hours. The reaction mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1 to 10:1) to give (2S)-2-((2S)-2 -hydroxy-3-phenoxypropylamino)-3-[4-(quinolin-3-yloxy) phenyl]-propan-1-ol (110 mg). NMR (DMSO-d6, δ):2.55-2.85 (5H, m), 3.2-3.5 (2H, m), 3.75-4.0 (3H, m), 6.85-6.95 (3H, m), 7.05 (2H, d, J=8.4 Hz),7.2-7.35 (4H, m), 7.5-7.75 (3H, m), 7.85-7.9 (1H, m), 8.02 (1H, d, J=8.3 Hz), 8.79 (1H, d, J=2.8 Hz)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 59
  • (S)-2-amino-3-[4-(quinolin-4-yloxy)phenyl]propan-1-ol dihydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • (2S)-2-[(2S)-2-hydroxy-3-phenoxypropylamino]-3-[4-(quinolin-4-yloxy)phenyl]propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With N-ethyl-N,N-diisopropylamine; In ethanol; ethyl acetate; Example 65 To a solution of (S)-2-amino-3-[4-(quinolin-4 -yloxy)-phenyl]propan-1-ol dihydrochloride (916 mg, 2.49 mmol) in ethanol (18 ml) was successively added (S)-3-phenoxy-1,2 -epoxypropane (374 mg, 2.49 mmol) and diisopropylethylamine (2.17 ml, 12.5 mmol) at room temperature and the whole was refluxed for 11 hours. After cooling to room temperature, the solvent was evaporated and the residue was dissolved in ethyl acetate (20 ml). The solution was washed with water (20 ml*2), brine (20 ml*1), dried (magnesium sulfate), and evaporated to give a crude oil (995 mg). The crude oil was chromatographed on a 50 g of silica gel (eluent: chloroform/methanol=9/1) to give (2S)-2-[(2S)-2-hydroxy-3 -phenoxypropylamino]-3-[4-(quinolin-4-yloxy)phenyl]propan-1-ol (306 mg, 28%) as a white solid. IR (KBr): 3421 (br, OH, NH), 1500, 1250, 1213 cm-1 NMR (CDCl3, delta):2.02 (3H, br), 2.80-3.06 (5H, m), 3.47 (1H, dd, J=5.1, 11.0 Hz), 3.71 (1H, dd, J=3.7, 11.0 Hz), 4.01 (3H, m), 6.54 (1H, d, J=5.2 Hz), 6.89-7.00 (3H, m), 7.13 (2H, d, J=8.4 Hz), 7.26-7.33 (4H, m), 7.55-7.81 (2H, m), 8.10 (1H, d, J=8.4 Hz), 8.36 (1H, d, J=7.5 Hz), 8.65 (1H, d, J=5.2 Hz) MS:445(M+1)
Reference： [1]Patent: US2002/143034,2002,A1
  • 60
  • (S)-2-amino-3-[4-(imidazo[1,2-a]-pyridin-5-yloxy)phenyl]propan-1-ol [ No CAS ]
  • [ 71031-03-3 ]
  • [ 282099-89-2 ]
YieldReaction ConditionsOperation in experiment
14% In ethanol; ethyl acetate 66 Example 66 Example 66 A solution of (S)-2-amino-3-[4-(imidazo[1,2-a]pyridin-5 -yloxy)phenyl]propan-1-ol (313 mg, 1.10 mmol) and (S)-3 -phenoxy-1,2-epoxypropane (198 mg, 1.32 mmol) in ethanol (6.0 ml) was refluxed for 4 hours. After cooling to room temperature, the solvent was evaporated and the residue was dissolved in ethyl acetate (20 ml). The solution was washed with water (20 ml*2), brine (20 ml*1), dried (magnesium sulfate), and evaporated to give an orange oil. The oil was chromatographed on a 50 g of silica gel (eluent: chloroform/methanol=95/5) to give a pale yellow oil (134 mg). Further purification was performed by a recycling preparative HPLC equipped with a GPC column (eluent: chloroform) to give 2(S)-2-[(2S)-2-hydroxy-3 -phenoxypropyl-amino]-3-[4-(imidazo[1,2-a]pyridin-5-yloxy)phenyl]propan-1-ol (67.5 mg, 14%) as a pale yellow oil. MS:434(M+1)
Reference： [1]Current Patent Assignee: HP INC.; ASTELLAS PHARMA INC. - US2002/143034, 2002, A1
  • 61
  • (S)-2-amino-3-[4-(7-chloroquinolin-4-yloxy)phenyl]propan-1-ol hydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • [ 282099-96-1 ]
YieldReaction ConditionsOperation in experiment
31% With diisopropylamine; In ethanol; ethyl acetate; Example 73 To a suspension of (S)-2-amino-3-[4-(7-chloroquinolin-4 -yloxy)phenyl]propan-1-ol hydrochloride (480 mg, 1.19 mmol) in ethanol (10 ml) were successively added diisopropylamine (0.518 ml, 2.97 mmol) and (S)-3-phenoxy-1,2-epoxypropane (197 mg, 1.31 mmol) at room temperature and the solution was refluxed for 2.5 hours. After cooling to room temperature, the solvent was removed by evaporation and the residue was suspended in ethyl acetate (50 ml). The mixture was washed with water (50 ml*1), brine (50 ml*1), dried (magnesium sulfate), and evaporated to give a yellow oil (480 mg). The crude oil was chromatographed on a 50 g of silica gel (eluent: chloroform/methanol=95/5) to give 2(S)-3-[4-(7 -chloroquinolin-4-yloxy)phenyl]-2-[(2S)-2-hydroxy-3 -(phenoxy)-propylamino]propan-1-ol (176 mg, 31%) as a white solid. IR (KBr): 3381, 1612, 1587, 1570, 1495, 1246, 1211 cm-1 NMR (CDCl3, delta):2.02 (3H, br s), 2.78-3.02 (5H, m), 3.47 (1H, dd, J=5.0, 10.8 Hz), 3.71 (1H, dd, J=3.3, 10.8 Hz), 4.01-4.05 (3H, m), 6.52 (1H, d, J=5.2 Hz), 6.89-7.00 (3H, m), 7.25-7.33 (4H, m), 7.53 (1H, dd, J=2.0, 8.9 Hz), 8.09 (1H, d, J=2.0 Hz), 8.30 (1H, d, J=8.9 Hz), 8.64 (1H, d, J=5.2 Hz) MS (m/z):479(M+1)
Reference： [1]Patent: US2002/143034,2002,A1
  • 62
  • N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine [ No CAS ]
  • [ 71031-03-3 ]
  • (2S)-1-[N-benzyl-N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amino]-3-phenoxy-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 13 EXAMPLE 13 EXAMPLE 13 Under nitrogen, to a solution of N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (258 mg) and (2S)-3-phenoxy-1,2-epoxypropane (138 mg) in dichloromethane (5 ml) was added ytterbium(III) trifluoromethanesulfonate (52 mg) at room temperature, and the mixture was stirred at the same temperature for 60 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1) to give (2S)-1-[N-benzyl-N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amino]-3-phenoxy-2-propanol (303 mg).
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2002/120148, 2002, A1
  • 63
  • 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)acetamide [ No CAS ]
  • [ 71031-03-3 ]
  • [ 246262-37-3 ]
YieldReaction ConditionsOperation in experiment
With methanesulfonic acid;ytterbium(III) triflate; In dichloromethane; chloroform; EXAMPLE 30 Under nitrogen, to a solution of 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)acetamide (260 mg) and (2S)-3-phenoxy-1,2-epoxypropane (130 mg) in dichloromethane (3 ml) was added ytterbium(III) trifluoromethanesulfonate (50 mg) at room temperature, and the mixture was stirred at the same temperature for 12 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=20:1 to 10:1), followed by treatment with methanesulfonic acid in chloroform to give 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetamide methanesulfonate (290 mg). (+) APCI-MASS (m/z): 475 (M-MsOH+H)+
Reference： [1]Patent: US2002/120148,2002,A1
  • 64
  • N-Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride [ No CAS ]
  • [ 71031-03-3 ]
  • [ 152356-06-4 ]
  • (2S)-1-[N-benzyl-N-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene 5 EXAMPLE 5 EXAMPLE 5 N-Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride was converted to the corresponding free base in a usual manner. A mixture of (2S)-3-phenoxy-1,2-epoxypropane (75 mg), N-benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (140 mg), and ytterbium(III) trifluoromethanesulfonate (93 mg) in toluene (2.6 ml) was stirred at room temperature for 3 days and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol) over silica gel to afford (2S)-1-[N-benzyl-N-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (200 mg). IR (KBr): 3427, 1248 cm-1 NMR (CDCl3, δ): 1.25-2.25 (4H, m), 2.5-3.02 (7H, m), 3.65-4.0 (8H, m), 6.63 (2H, m), 6.83-6.98 (3H, m), 7.03-7.08 (1H, m), 7.18-7.31 (7H, m) MASS (m/z): 432 (M+H)+
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2002/120148, 2002, A1
  • 65
  • N-benzyl-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine [ No CAS ]
  • [ 71031-03-3 ]
  • (2S)-1-[N-benzyl-N-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 67 EXAMPLE 67 EXAMPLE 67 Under nitrogen, to a solution of N-benzyl-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (440 mg) and (2S)-1-phenoxy-2,3-epoxypropane (190 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (157 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford (2S)-1-[N-benzyl-N-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (400 mg).
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2002/120148, 2002, A1
  • 66
  • [ 29968-78-3 ]
  • [ 71031-03-3 ]
  • [ 202740-27-0 ]
YieldReaction ConditionsOperation in experiment
In triethylamine; REFERENTIAL EXAMPLE 8 7.71 g of (S)-2-phenoxymethyloxirane and 10.34 g of 2-(4-nitrophenyl)ethylamine hydrochloride were subjected to a ring-opening reaction in the presence of 5.20 g of triethylamine to obtain 6.35 g of (S)-1-phenoxy-3-[[2-(4-nitrophenyl)ethyl]amino]-2-propanol.
Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3283 - 3294
[2]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 139 - 145
[3]Patent: US6048884,2000,A
  • 67
  • [ 71031-03-3 ]
  • [ 103-49-1 ]
  • of(2S)-2-(phenoxymethyl)oxirane [ No CAS ]
  • [ 437764-00-6 ]
YieldReaction ConditionsOperation in experiment
88% In methanol; EXAMPLE 48 Preparation of (2S)-1-(dibenzylamino)-3-phenoxy-2-propanol A reaction mixture containing (2S)-2-(phenoxymethyl)oxirane (Example 15, 20.6 mmol, 1.0 eq.) and dibenzylamine (22.7 mmol, 1.1 eq.) in MeOH (100 mL) was heated at reflux overnight. The resulting solution was concentrated in vacuo and the crude product was purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, hexanes:EtOAc=10:1). The product was obtained as a colorless oil in 88% yield. MH+=348.3, Rf=0.42 (hexanes:EtOAc 6:1), retention time (LC-MS)=2.22 min. By using the appropriately substituted epoxide in place of(2S)-2-(phenoxymethyl)oxirane, the following compounds were prepared and characterized according to method of Example 48.
Reference： [1]Patent: US2003/78258,2003,A1
  • 68
  • [ 115314-14-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
81.1% (R)-2-phenoxymethyl-oxirane Add phenol (1.089 g, 11.572 mmol) to a slurry of sodium hydride (0.347 g, 14.465 mmol) in N,N-dimethylformamide (77.1 mL) and stir at room temperature for 40 minutes. Add 3-nitrobenzenesulfonic acid (R)-1-oxiranylmethyl ester (3.00 g, 11.572 mmol) and stir at room temperature for 16 hours (J. Org. Chem., 54, 1296-1304 (1989). Quench with saturated aqueous ammonium chloride (75 mL), dilute with water (75 mL) and extract with diethyl ether (3*300 mL). Combine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL), dry (magnesium sulfate), filter and purify (silica gel chromatography, eluding with 10:90 to 50:50 ethyl acetate:hexanes) to give the desired compound as a clear liquid (1.410 g, 81.1%). GC-MS=150 [M]
Reference： [1]Patent: US2007/225267,2007,A1 .Location in patent: Page/Page column 43
  • 69
  • [ 1092363-44-4 ]
  • [ 71031-03-3 ]
  • [ 1092363-49-9 ]
Reference： [1]Synlett,2008,p. 2451 - 2454
  • 70
  • [ 1092363-46-6 ]
  • [ 71031-03-3 ]
  • [ 1092363-51-3 ]
Reference： [1]Synlett,2008,p. 2451 - 2454
  • 71
  • 4'-(2-aminoethyl)-2-(2-pyridyl)acetanilide [ No CAS ]
  • [ 71031-03-3 ]
  • [ 1160961-92-1 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 4'-(2-aminoethyl)-2-(2-pyridyl)acetanilide; (R)-phenyl glycidyl ether With triethylamine In isopropyl alcohol at 70℃; for 2h; Stage #2: With hydrogenchloride In 1,4-dioxane; acetone
Reference： [1]Location in patent: experimental part Maruyama, Tatsuya; Onda, Kenichi; Hayakawa, Masahiko; Seki, Norio; Takahashi, Takumi; Moritomo, Hiroyuki; Suzuki, Takayuki; Matsui, Tetsuo; Takasu, Toshiyuki; Nagase, Itsuro; Ohta, Mitsuaki [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3283 - 3294]
  • 72
  • [ 211103-68-3 ]
  • [ 71031-03-3 ]
  • (S)-N-methyl-4'-{2-[(2-hydroxy-3-phenoxypropyl)-amino]ethyl}-2-(1-benzylimidazol-2-yl)acetanilide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: 4'-(2-aminoethyl)-2-(1-benzylimidazol-2-yl)-N-methyl-acetanilide; (R)-phenyl glycidyl ether In isopropyl alcohol at 90℃; for 22h; Stage #2: With hydrogenchloride In methanol; ethyl acetate
Reference： [1]Location in patent: experimental part Maruyama, Tatsuya; Onda, Kenichi; Hayakawa, Masahiko; Seki, Norio; Takahashi, Takumi; Moritomo, Hiroyuki; Suzuki, Takayuki; Matsui, Tetsuo; Takasu, Toshiyuki; Nagase, Itsuro; Ohta, Mitsuaki [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3283 - 3294]
  • 73
  • [ 124-38-9 ]
  • [ 122-60-1 ]
  • [ 1070894-44-8 ]
  • [ 184343-68-8 ]
  • [ 71031-03-3 ]
  • [ 71031-03-3 ]
Reference： [1]Bulletin of the Chemical Society of Japan,2007,vol. 80,p. 1391 - 1401
[2]Organic Letters,2017,vol. 19,p. 4070 - 4073
[3]Organic Letters,2019,vol. 21,p. 1853 - 1856
  • 74
  • [ 1192-04-7 ]
  • [ 71031-03-3 ]
  • [ 1177441-31-4 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3362 - 3365
  • 75
  • [ 103559-91-7 ]
  • [ 71031-03-3 ]
  • [ 1177441-09-6 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3362 - 3365
  • 76
  • [ 13291-18-4 ]
  • [ 71031-03-3 ]
  • [ 1177441-30-3 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3362 - 3365
  • 77
  • [ 5674-01-1 ]
  • [ 71031-03-3 ]
  • [ 1177441-43-8 ]
Reference： [1]Organic Letters,2009,vol. 11,p. 3362 - 3365
  • 78
  • [ 71031-03-3 ]
  • [ 121751-67-5 ]
  • [ 1005791-37-6 ]
YieldReaction ConditionsOperation in experiment
50% In methanol; for 24h;Reflux; Inert atmosphere; A solution of 1-(4-methoxybenzenesulfonyl)piperazine (717 mg, 2.8 mM) and (S)-(hetero)aryloxymethyloxirane (2 mM) (prepared using known process) in anhydrous methanol (20 ml) is refluxed in a nitrogen atmosphere up to completion. The solvent is then removed under vacuum. The crude product is dissolved in ethyl acetate and the organic phase is washed with water, dried on anhydrous Na2SO4, filtered and the solvent removed under vacuum.;The process followed is the same as described in Example 23.Time of the reaction: 24 h. The product is isolated as a white solid in (yield of 50%) by column chromatography (silica gel, mobile phase: petroleum ether/ethyl acetate=6:4 and then 1:1) of the crude reaction product. Pf 136.0-138.0 C. (CH Cl3/hexane). [alpha]D=-11.7 (c 0.98, CHCl3). FT-IR (KBr): 3496, 3030, 2950, 2851, 2819, 1600, 1577, 1500, 1465, 1345, 1331, 1303, 1248, 1136, 1112, 1095, 1040, 1022, 998, 990, 950, 884, 847, 816, 806, 752, 733, 693 cm-1. 1NMRs (300 MHz CDCl3, delta): 7.72-7.67 (m, 2H, aromatic protons); 7.29-7.23 (m, 21-1, aromatic protons); 7.03-6.98 (m, 2H, aromatic protons); 6.97-6.92 (m, 1H, aromatic proton); 6.90-6.86 (m, 2H, aromatic protons), 4.08-4.02 (m, 1H, CHOH); 3.94-3.92 (m, 2H, C6H50CH2); 3.88 (s, 3H, OCH3); 3.20-2.90 (bs, 5H, OH exchange with D2O, and 2 CH2N of piperazine); 2.79-2.72 (m, 2H, CH2N of piperazine); 2.63-2.53 (m, 4H, CH2N of piperazine and CHOHCH2N). 13C NMRs (75 MHz CDCl3, delta): 163.41, 158.75, 130.15, 129.71, 127.19, 121.37, 114.74, 114.53, 77.46, 70.15, 66.03, 60.51, 55.87, 52.72, 46.21. MS-ESI m/z (%): 407 [M+H]+(10); 429 [M+Na]+(100). Anal. Calc. for C20H26N2O5S: C, 59.09; H, 6.45; N, 6.89. Found: C, 59.38; H, 6.33; N, 7.03.
Reference： [1]Patent: US2010/75977,2010,A1 .Location in patent: Page/Page column 8
  • 79
  • [ 71031-03-3 ]
  • (S)-1-Phenoxypropan-2-ol [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2825 - 2829
  • 80
  • [ 71031-03-3 ]
  • (S)-1-iodo-3-phenoxy-2-hydroxypropane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trimethylsilyl iodide; triphenylphosphine; In chloroform; EXAMPLE 8 (S)-1-Iodo-2-hydroxy-3-phenoxypropane To a rapidly stirring, cooled (ice water bath) mixture of 37.5 g (0.25 mol) of R-glycidol phenyl ether and 0.655 g (2.5 mmol) of triphenylphosphine in 200 ml of ethanol free chloroform is added slowly via a syringe 50 g (0.250 mol) of iodotrimethylsilane. The chloroform is washed with 200 ml of 10% aqueous sodium thiosulfate, brine, and dried over magnesium sulfate. Isolation in vacuo affords the title compound.
Reference： [1]Patent: US4322557,1982,A
  • 81
  • [ 18303-04-3 ]
  • [ 71031-03-3 ]
  • (S)-1-(4-methylphenylsulfonamido)-3-phenoxypropan-2-yl tert-butylcarbonate [ No CAS ]
  • C25H29NO6S [ No CAS ]
  • (S,S)-(1-(N-(2-hydroxy-3-phenoxypropyl)-4-methylphenylsulfonamido)-3-phenoxypropan-2-yl) tert-butylcarbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 5% 3: 8% With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 6h;
Reference： [1]Location in patent: experimental part Albanese, Domenico; Landini, Dario; Penso, Michele; Tagliabue, Aaron; Carlini, Emanuele [Organic Process Research and Development, 2010, vol. 14, # 3, p. 705 - 711]
  • 82
  • [ 2133-07-5 ]
  • [ 71031-03-3 ]
  • [ 1403506-15-9 ]
YieldReaction ConditionsOperation in experiment
Example 11:(S)-l-Benzyl-2-phenoxymethylmorpholine (Compound D) A solution of NaOH (572 g, 14.3 mol) in water (1L) was cooled to 10-15 C. To this was added N-benzyl ethanolamine hydrogen sulphate (368 g, 1.591 mol) (C) while maintaining the temperature less than 20 C. The mixture was stirred at room temperature for 10 min. A solution of (S)-2-(phenoxymethyl)oxirane (A) (216 g, 1.438 mol) in toluene was added over 10-15 min. The mixture was stirred at 45-50 C for 16 h. On completion of the reaction, water (2 L) and EtOAc (2 L) was added to the reaction mixture. The organic layer was separated and washed with water and extracted with 10 % aqueous HC1 (2 L). The combined HC1 washings were basified with NaOH to pH 9 and extracted with EtOAc (2.1 L). The EtOAc extract was washed with water (1 L), brine (1 L), dried over anhydrous Na2S04 and concentrated completely to afford the title compound.*H NMR (300 MHz, CDC13): delta 7.33-7.23 (m, 7H), 6.96-6.93 (d, J = 7.5 Hz, 1H), 6.90-6.88 (d, J = 8.1 Hz , 2H), 4.05-3.90 (m, 4H), 3.77-3.66 (t, J = 11.1 Hz, 1H), 3.55 (s, 2H), 3.49- 2.86 (d, J = 11.1 Hz, 1H), 2.70-2.66 (d, J = 11.1 Hz, 1H), 2.274-2.187 (t, J = 11.4 Hz, 1H), 2.131-2.063 (t, J = 9.6 Hz, 1H); MS: m/z 284 (M+H)+.
Reference： [1]Patent: WO2012/143874,2012,A1 .Location in patent: Page/Page column 35-36
  • 83
  • [ 51594-55-9 ]
  • [ 108-95-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; at 20 - 100℃; for 1h; Example 9:(S)-2-Phenoxymethyloxirane (Compound A)To a solution of NaOH (91.2 g, 2.28 mol) and phenol (143 g, 1.52 mol) in water (1.8 L), at room temperature was added tetrabutylammonium hydrogensulphate (1.5 g, 0.0044 mol). R- epichlorohydrin (662 g, 7.15 mol) was added slowly over a period of 10-15 min along with vigorous stirring. The mixture was stirred vigorously at 90-100 C for 1 h. On completion of the reaction, it was extracted with 1 : 1 ethyl acetate: petroleum ether (1 L). The combined organic layer was concentrated below 40 C to remove the solvent. The residue was distilled and the fraction from 115-125 C at 2 mm (diaphragm pump) was collected (maintaining the oil bath temperature at 155-160 C) to afford the title compound.*H NMR (300 MHz, CDC13): delta 7.28-7.34 (m, 2H), 6.93-7.03 (m, 3H), 4.255 (m, 1H), 4.00 (m, 1H), 3.390 (t, 1H), 2.95 (m, 1H), 2.785 (m, 1H); MS: m/z 151 (M+H).
Reference： [1]Patent: WO2012/143874,2012,A1 .Location in patent: Page/Page column 35
  • 84
  • [ 71031-03-3 ]
  • [ 65838-10-0 ]
  • [ 1415402-88-8 ]
YieldReaction ConditionsOperation in experiment
82.5% In methanol; at 60℃; for 24h;Inert atmosphere; (S)-Phenyl glycidyl ether (1.53 g, 10.2 mmol) was added to a solution of (R,R)-N,N'-dibenzyl-1,2-diaminocylohexane (1) (1.5 g, 5.1 mmol) in methanol (4 mL) at 60 C for 24 h. Solvent was evaporated then the crude product was purified by crystallization from n-hexane-ethanol to give 4 (2.5 g, 82.5%) as a white solid, mp 83-85 C; [alpha]D20 -53 (c 1, EtOH); [found: C: 76.52, H: 7.52, N: 4.91. C38H46N2O4 requires C: 76.74, H: 7.80, N: 4.71%]; numax (KBr) 3360, 3169, 3060, 3028, 2929, 2855, 1600, 1496, 1455, 1373, 1302, 1274, 1120, 1080, 1036, 935, 884, 813, 754, 693 cm-1; deltaH (400 MHz, CDCl3) 7.45-7.05 (10H, m), 5.6 (2H, bs, OH), 4.36-3.79 (4H, m), 3-2.68 (3H, m), 2.31-1.92 (3H, m), 1.26 (2H, bs); deltaC (100 MHz, CDCl3) 158.8, 138.3, 129.9, 129.5, 128.9, 128.4, 120.9, 114.7, 70.5, 67.1, 58.7, 56.3, 52.2, 25.7, 24.3.
Reference： [1]Tetrahedron,2013,vol. 69,p. 349 - 358
  • 85
  • [ 124-38-9 ]
  • [ 71031-03-3 ]
  • [ 184343-68-8 ]
Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 15578 - 15589
[2]ACS Catalysis,2016,vol. 6,p. 6906 - 6910
[3],2020,vol. 10,p. 3265 - 3278
[4]Journal of the American Chemical Society,2013,vol. 135,p. 18497 - 18501
[5]Journal of Organic Chemistry,2014,vol. 79,p. 9771 - 9777
  • 86
  • [ 71031-03-3 ]
  • [ 64-04-0 ]
  • N-(2-phenylethyl)-4-aza-1,7-diphenoxy-(2S,6S)-2,6-dihydroxyheptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.2% In methanol; at 60℃; for 24h;Inert atmosphere; (S)-Glycidyl phenyl ether (119mg, 7.92mmol) was added to a solution of 2-phenylethylamine (480mg, 3.96mmol) in methanol (3 ml) and stirred at 60C for 24 h. The solution was concentrated under reduced pressure. Then, the excess epoxide and amine were removed using a Kugelrohr distillation apparatus to afford 2 (1.6 g, 95.2%) as colourless oil. [Found: C: 74.08%, H: 7.41%, N: 3.32%. C26H31NO4 requires C: 74.22%, H: 7.84%, N: 3.55%]; [alpha]20D 35.3(c 1, EtOH); numax (liquid film): 3390, 3061, 3028, 2933,2870, 2827, 1704, 1597, 1494, 1457, 1334, 1296, 1245,1173, 1118, 1081, 1040, 910, 882, 818, 753, 695, 486 cm-1; deltaH (400MHz, CDCl3): 7.41-7.01 (m, 10H), 4.20-3.92 (m,5H), 3.06-2.83 (m, 5H). deltaC (100MHz, CDCl3): 158.79,140.17, 129.67, 128.93, 128.68, 126.34, 121.18, 114.74,70.10, 67.64, 57.58, 57.51, 33.52.
Reference： [1]Supramolecular Chemistry,2014,vol. 26,p. 363 - 372
  • 87
  • [ 71031-03-3 ]
  • [ 3850-30-4 ]
  • N-[(S)-(1)-3,3-dimethyl-2-butyl]-4-aza-1,7-diphenoxy-(2S,6S)-2,6-heptanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In methanol; at 60℃; for 24h;Inert atmosphere; (S)-Glycidyl phenyl ether (1.8 g, 12 mmol) was added to a solution of R-(3,3)-dimethyl-2-butylamine (0.6 g, 6 mmol) in methanol (3 ml) stirred at 60C for 24 h. The solution was concentrated under reduced pressure. The residue was purified by silica-gel CC (n-hexane:EtOAc, 2:1), to afford 4 (2 g, 83%) as a colourless oil. [Found: C: 71.79%, H:8.79%, N: 3.49%. C24H35NO4 requires C: 72.02%, H:8.93%, N: 3.42%]; [alpha]20D -7.1 (c 1, CHCl3); numax (liquid film): 3396, 3060, 3038, 2951, 2868, 2541, 2478,1600, 1497, 1468, 1364, 1335, 1291, 1247, 1172, 1078,1041, 881, 828, 753, 692 cm-1; deltaH (400 MHz, CDCl3):7.36-7.32 (m, 4H), 7.04-6.97 (m, 6H), 4.16-4.11 (m,4H), 4.09-3.99 (d, 5.2 Hz, 4H, -CH2OPh), 2.70-2.67 (m,4H), 2.46-2.41 (q, 6.8 Hz, 1H), 1.12-1.10 (m, 12H); deltaC(100 MHz, CDCl3): 158.86, 129.56, 121.04, 114.69, 67.5,65.83, 55.22, 35.44, 28.06, 8.26.
Reference： [1]Supramolecular Chemistry,2014,vol. 26,p. 363 - 372
  • 88
  • [ 140630-45-1 ]
  • [ 538-43-2 ]
  • [ 71031-03-3 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide In aq. phosphate buffer for 0.5h; Enzymatic reaction; Scale-up preparation of (R)-SO and (S)-PGE Scale-up preparation of (R)-SO and (S)-PGE The reaction started at 30 °C by adding 624 mg a-chloroacetophe-none or 738 mg 3-chloro-1-phenoxy-2-propanone into 100 ml PBSbuffer (pH7.6) containing 100 mg/ml KcDH resting cell, 1 ml iso-propanol, and 20 mg NAD. After bio-reduction was completed,2.5 ml of 6 M NaOH was added for epoxidation. The epoxidationwas terminated after 30 min by neutralisation with 6 M HCl. The pro-duct SO and PGE was extracted with hexane three times. After dryingover anhydrous sodium sulphate, solvents were removed under vac-uum. The obtained SO and PGE were analysed by chiral HPLC andGC, and the spectral data are presented in Supplemental material.
Reference： [1]Wu, Kai; Chen, Lifeng; Fan, Haiyang; Zhao, Zhiqiang; Wang, Hualei; Wei, Dongzhi [Tetrahedron Letters, 2016, vol. 57, # 8, p. 899 - 904]

Tags: 71031-03-3 synthesis path| 71031-03-3 SDS| 71031-03-3 COA| 71031-03-3 purity| 71031-03-3 application| 71031-03-3 NMR| 71031-03-3 COA| 71031-03-3 structure

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