(R)-2-AMINO-1,2-DIPHENYL-1-PROPANOL

white to light yellow crystal powde

(R)-2-amino-l, l-diphenyl-propan-l-ol A solution of PhMgBr (0.87 mol in 287 mL THF) was cooled to 0 °C under inert atmosphere. (R)- 1-Methoxycarbonyl-ethyl-ammonium chloride (20 g, 140 mmol) was charged in portions over a period of 90 min to maintain the temperature between 0 and 5 °C. The reaction mixture was stirred for 30 min between 0 and 5 °C and then allowed to warm to RT. After 4 h at RT, the mixture was cooled to 0 °C. Aqueous HC1 (100 mL, 10 percent w/w) was added over a period of 60 min between 0 and 5 °C. The mixture was warmed to RT. Ethyl acetate (300 mL) and water (400 mL) were charged. The phases were separated and the water phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed successively with water (50 mL) and brine (50 mL). The organic phase was concentrated under vacuum to afford a residue (about 50 g). Hexane (30 mL) was charged in 30 min. The mixture was cooled down to 0 °C in 3 h and then aged for 1 h at 0 °C. The mixture was filtered to afford after isolation and drying (R)-2-amino-l, l-diphenyl-propan-l-ol (30.4 g, 80 percent yield) as a yellow solid. 1H NMR (400 MHz, CDC1 (R)-2-amino-l, l-diphenyl-propan-l-olA solution of PhMgBr (0.87 mol in 287 mL THF) was cooled to 0 °C under inert atmosphere. (R)-l-Methoxycarbonyl-ethyl-ammonium chloride (20 g, 140 mmol) was charged in portions over a period of 90 min to maintain the temperature between 0 and 5 °C. The reaction mixture was stirred for 30 min between 0 and 5 °C and then allowed to warm to RT. After 4 h at RT, the mixture was cooled to 0 °C. Aqueous HCl (100 mL, 10 percent w/w) was added over a period of 60 min between 0 and 5 °C. The mixture was warmed to RT. Ethyl acetate (300 mL) and water (400 mL) were charged. The phases were separated and the water phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed successively with water (50 mL) and brine (50 mL). The organic phase was concentrated under vacuum to afford a residue (about 50 g). Hexane (30 mL) was charged in 30 min. The mixture was cooled down to 0 °C in 3 h and then aged for 1 h at 0 °C. The mixture was filtered to afford after isolation and drying (R)-2-amino-l, l-diphenyl-propan-l-ol (30.4 g, 80 percent yield) as a yellow solid.1H NMR (400 MHz, CDCI3) delta 7.64 (dd, J = 7.6, 4.0 Hz, 2 H), 7.51 (dd, J = 7.6, 1.4 Hz, 2 H), 7.37 to 7.28 (m, 4 H), 7.24 to 7.17 (m, 2 H), 4.18 (q, J = 6.3 Hz, 1 H), 0.99 (d, J = 6.3 Hz, 3 H). (R)-2-amino-l, l-diphenyl-propan-l-olA solution of PhMgBr (0.87 mol in 287 mL THF) was cooled to 0 °C under inert atmosphere. (R)-l-Methoxycarbonyl-ethyl-ammonium chloride (20 g, 140 mmol) was charged in portions over a period of 90 min to maintain the temperature between 0 and 5 °C. The reaction mixture was stirred for 30 min between 0 and 5 °C and then allowed to warm to RT. After 4 h at RT, the mixture was cooled to 0 °C. Aqueous HCl (100 mL, 10 percent w/w) was added over a period of 60 min between 0 and 5 °C. The mixture was warmed to RT. Ethyl acetate (300 mL) and water (400 mL) were charged. The phases were separated and the water phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed successively with water (50 mL) and brine (50 mL). The organic phase was concentrated under vacuum to afford a residue (about 50 g). Hexane (30 mL) was charged in 30 min. The mixture was cooled down to 0 °C in 3 h and then aged for 1 h at 0 °C. The mixture was filtered to afford after isolation and drying (R)-2-amino-l, l-diphenyl-propan-l-ol (30.4 g, 80 percent yield) as a yellow solid.1H NMR (400 MHz, CDCI3) delta 7.64 (dd, J = 7.6, 4.0 Hz, 2 H), 7.51 (dd, J = 7.6, 1.4 Hz, 2 H), 7.37 to 7.28 (m, 4 H), 7.24 to 7.17 (m, 2 H), 4.18 (q, J = 6.3 Hz, 1 H), 0.99 (d, J = 6.3 Hz, 3 H).

Molecular Weight:227.30
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:227.131014166
Monoisotopic Mass:227.131014166
Topological Polar Surface Area:46.2
Heavy Atom Count:17
Complexity:211
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes