2-(benzyl(methyl)amino)-1-phenylethanol

In a high-purity argon atmosphere, [Ir (COD) Cl] 2 (1.34 mg, 2 mummol) and a chiral ligand (2.32 mg, R = tBu, 4 mummol) were dissolved in isopropanol (2 mL).After stirring at room temperature for 3 hours, a clear orange solution was obtained. Take 100 muL of orange clear solution and dilute to 10 times volume with isopropanol.Take 20 muL (0.002 mol%) of this orange solution with a micro syringe, and add to 2- (benzyl (methyl) amine) -1-acetophenone hydrochloride (0.2 mmol), In a mixed system of isopropanol (2 mL) and potassium tert-butoxide (1.3 mol%). The reaction system was placed in an autoclave and stirred at room temperature under H2 (40 atm) conditions for 12 hours.The solvent was removed under reduced pressure, and column chromatography was performed (silica gel column was used, eluent: ethyl acetate), Pure 2- (benzyl (methyl) amine) -1-phenylethanol was obtained, and the product was analyzed by HPLC to determine the ee value (ee> 99%).General procedure: A mixture of the substituted benzaldehyde (1.0mmol), finelyground sarcosine (0.13 g, 1.5 mmol), and paraformaldehyde (0.09g, 3.0 mmol)was refluxedin dry benzene (3.3 mL), with magnetic stirring and removal of formed water by means of a Dean-Starktrap, for 6-8h. The resulting solution was evaporated in vacuo to give the oily 5-aryl-3-methyloxazolidine 6. This was dissolved in toluene (1 mL)and quickly added to asolution of ArMgBr prepared from ArBr (1.5 mmol)and Mg (0.04g, 1.5 mmol)in THF (2mL)at 0 C with vigorous stirring. The mixture was left overnight at room temperature. Concentrated HCl (0.25 mL, 3.0 mmol)and toluene (3mL)were added with stirring to the cooled solution ( 5 C). The organic layer was decanted and the precipitate additionally washed with toluene and Et 2O. After basification with an excess of aq NH 3, extraction with CH 2Cl2 (2 2 mL), drying over Na 2SO4, and evaporation, the corresponding N-benzyl-b-hydroxyphenethylamine 7 was obtained. This was dissolved in CH 2Cl2 (2 mL)and treated dropwise with concd H2SO4 (2 mL)(96%-for 7a, b, 75%-for 7d, e) over 5min. After stirring for 2h, ice chips were added and the aq solution made basic with aq NaOH solution. The mixture was extracted with CH 2Cl2 (2 2 mL)and the combined organic extracts dried over anhydrous Na 2SO4, filteredthrough athin layer of silica gel and concentrated in vacuo. Amino alcohols 7c and 7f were cyclized using AlCl 3 in CH 2Cl2 (4.0 equiv, reflux, 1.5 h)and polyphosphoric acid (1.1gof PPA- 1 mmol of 7f, 80-90 C, 1.5 h), respectively. The free bases were converted into hydrochloride salts with anhydrous ethereal HCl solution generated in situ from i-PrOH (1.3 equiv)and AcCl (1.1equiv).General procedure: A mixture of the substituted benzaldehyde (1.0mmol), finelyground sarcosine (0.13 g, 1.5 mmol), and paraformaldehyde (0.09g, 3.0 mmol)was refluxedin dry benzene (3.3 mL), with magnetic stirring and removal of formed water by means of a Dean-Starktrap, for 6-8h. The resulting solution was evaporated in vacuo to give the oily 5-aryl-3-methyloxazolidine 6. This was dissolved in toluene (1 mL)and quickly added to asolution of ArMgBr prepared from ArBr (1.5 mmol)and Mg (0.04g, 1.5 mmol)in THF (2mL)at 0 C with vigorous stirring. The mixture was left overnight at room temperature. Concentrated HCl (0.25 mL, 3.0 mmol)and toluene (3mL)were added with stirring to the cooled solution ( 5 C). The organic layer was decanted and the precipitate additionally washed with toluene and Et 2O. After basification with an excess of aq NH 3, extraction with CH 2Cl2 (2 2 mL), drying over Na 2SO4, and evaporation, the corresponding N-benzyl-b-hydroxyphenethylamine 7 was obtained. This was dissolved in CH 2Cl2 (2 mL)and treated dropwise with concd H2SO4 (2 mL)(96%-for 7a, b, 75%-for 7d, e) over 5min. After stirring for 2h, ice chips were added and the aq solution made basic with aq NaOH solution. The mixture was extracted with CH 2Cl2 (2 2 mL)and the combined organic extracts dried over anhydrous Na 2SO4, filteredthrough athin layer of silica gel and concentrated in vacuo. Amino alcohols 7c and 7f were cyclized using AlCl 3 in CH 2Cl2 (4.0 equiv, reflux, 1.5 h)and polyphosphoric acid (1.1gof PPA- 1 mmol of 7f, 80-90 C, 1.5 h), respectively. The free bases were converted into hydrochloride salts with anhydrous ethereal HCl solution generated in situ from i-PrOH (1.3 equiv)and AcCl (1.1equiv).

Molecular Weight:241.33
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:241.146664230
Monoisotopic Mass:241.146664230
Topological Polar Surface Area:23.5
Heavy Atom Count:18
Complexity:219
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes