4-Piperidinemethanol → (1-{4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}piperidin-4-yl)-methanol

Participants

Reaction Steps

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbaldehyde (700 mg, 2.205 mmol, 1 wt), 4-piperidinemethanol (485 mg, 4.21 mmol), absolute ethanol (28 ml, 40 vol), activated 3 Å molecular sieves (700 mg), titanium (IV) isopropoxide (3.25 ml, 11.03 mmol) and STAB (3.97 g, 18.7 mmol) was reacted in accordance with the general procedure D. The isolated waxy solid was purified by column chromatography on silica eluting with DCM:MeOH:NH3 95:4:1 to give the title compound as a colorless oil (820 mg, 72%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.85 (d, 2H), 4.02 (t, 2H), 3.75 (dt, 2H), 3.59-3.46 (m, 2H), 3.42 (d, 2H), 2.63 (t, 2H), 2.53 (br s, 4H), 2.39-2.26 (m, 4H), 2.15-1.03 (m, 18H).

Provenance & Evidence