G 131 synthesis

Yield:36981-91-6 23%

Reaction Conditions:

Heating / reflux;

Steps:

2

Example 2 2-(2-phenyl-2-hydroxyethylamino)-2-methyl-propan-1-ol EPO ψ To a 250 ml 3-necked flask equipped with magnetic stirrer, reflux condenser, pressure equalizing dropping funnel and under nitrogen was charged 2-amino-2-5 methyl-1-propanol (10.0 ml, 0.112 mol). Styrene oxide (7.21 ml, 0.05 mol) was added dropwise and. the solution was heated overnight, (external oil bath temperature105⁰C). TLC analysis 95:5 (DCM: MeOH) indicated no starting material present.After cooling to room temperature, the precipitated solid was dissolved in boiling ethanol. Petroleum ether (few mis) was added to the stirring solution and a 10 white solid precipitated out. This was collected by filtration, and the crude product was purified by recrystallisation in boiling water. A white solid was afforded (5.30 g, 23.0%). NMR and LCMS analysis were consistent with the desired product. Further crops of the pure material could be obtained from the aqueous filtrate if necessary.¹H NMR (500MHz, MeOD) δ=1.07 (s, 6H, 2x CH₃), 2.69-2.77 (m, 2H, NCH₂), 15 3.32-3.35 (d, 1H, J = 11Hz CH₂O), 3.41-3.43 (d, 1H, J = 11 Hz, CH₂O), 4.71-4.74 (dd, 1H, J = 4.2 Hz, J = 8.7Hz, CH), 7.26-7.41 (m 5H, Ar).¹³C NMR spectrum (125MHz, MeOD) δ= 23.22, 24.07, 50.69, 54.69, 69.28, 74.40, 127.07, 128.61 , 129.42, 144.71.

References:

WO2007/3896,2007,A1 Location in patent:Page/Page column 8