Aluminium lithium hydride → Methyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-ylmethyl}amine

Participants

Reaction Steps

To a stirred solution of LiAlH4 (2.59 g, 68.18 mmol) in dry THF at 0° C. was added dropwise a solution of methyl-{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-pyran-4-ylmethyl}carbamic acid tert-butyl ester (9.50 g, 22.72 mmol). The reaction mixture was then brought to room temperature and finally heated to reflux for 3 h. The reaction mixture was quenched with aqueous NaOH solution and filtered over a short pad of celite, dried over Na2SO4 and concentrated under reduced pressure to provide the title compound (7.1 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ 1.71-1.78 (m, 4H); 1.80-1.90 (m, 2H); 1.88-2.02 (m, 2H); 2.06-2.14 (m, 2H); 2.23 (s, 3H); 2.46-2.53 (m, 4H); 2.51-2.63 (m, 4H); 3.47-3.56 (m, 2H); 3.70-3.77 (m, 2H); 3.99 (t, 2H); 6.86 (d, 2H); 7.17 (d, 2H).

Provenance & Evidence