2-Methyl-1-(tetrahydro-pyran-4-ylamino)-propan-2-ol synthesis

Yield:1178195-37-3 2.8 g

Reaction Conditions:

Stage #1: Tetrahydro-4H-pyran-4-one;1-Amino-2-methyl-propan-2-olwith acetic acid in methanol at 20; for 0.5 h;Inert atmosphere;
Stage #2: with methanol;sodium cyanoborohydride for 15 h;Inert atmosphere;

Steps:

14.1 Step 14.1 : (preparation of a compound of formula (XI)) 2-Methyl-1 -((tetrahydro-2H-pyran-4-yl)amino)propan-2-ol

Step 14.1 : (preparation of a compound of formula (XI)) 2-Methyl-1 -((tetrahydro-2H-pyran-4-yl)amino)propan-2-ol 2.75 g of 1-amino-2-methylpropan-2-ol are dissolved in 20 ml of MeOH. 1 .71 ml of glacial acetic acid are added dropwise under an inert atmosphere. 2 g of tetrahydropyran- 4-one in 10 ml of MeOH are added, the mixture is stirred for 30 minutes at room temperature and 1.98 g of sodium cyanoborohydride are added. The resulting mixture is stirred under an inert atmosphere for 15 hours. The reaction medium is poured into saturated aqueous NaHC0₃ solution (100 ml). The resulting mixture is stirred for 30 minutes and then extracted with 4 times 100 ml of DCM. The organic phase is dried over Na₂S0₄, filtered and evaporated without heating. The MeOH contained in the aqueous phase is evaporated off and the extraction, drying, filtration and evaporation operation is repeated 3 times. 2.8 g of 2-methyl-1 -((tetrahydro-2H-pyran-4-yl)amino)propan-2-ol are recovered in total.

References:

WO2013/111106,2013,A1 Location in patent:Page/Page column 97