N,N-dimethyl-N-((2Z)-3-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}prop-2-enyl)amine → 2-({2-[3-(Dimethylamino)propyl]pyridin-3-yl}oxy)ethanol
Reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3]/[CH:4]=[CH:5]\[C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15]C2CCCCO2)=[CH:10][CH:9]=[CH:8][N:7]=1>CO.[Pd]>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][N:7]=1Participants
4
Procedure
To a mixture of the cis and trans isomers N,N-dimethyl-N-((2E and 2Z)-3-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}prop-2-enyl)amine (from Example 20, Step 2; 3.1 g, 10.1 mmol) in MeOH (50 mL) was added 10% Pd/C (0.30 g) and the mixture was hydrogenated in a Parr apparatus at room temperature at 70 psi H2 overnight. The solvent from the filtered solution was removed under reduced pressure and the tetrahydropyranyl protecting group was removed using the procedure described in Example 19, Step 4, to yield 1.29 g (57%) of the title compound as a brown oil. HRMS m/z calcd for C12H20N2O2 (M)+ 224.1525. found 224.1521.