Sodium Bicarbonate → HCID 22137413, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-benzyloxy-phenyl)-[3-(tetrahydro-pyran-2-yloxy)-benzylidene]-amine (21.0 g, 54.2 mmol) in 350 mL methanol and 150 mL methylene chloride at 0° C. was added sodium borohydride (3.3 g, 86.7 mmol) in portions over 20 minutes. The reaction mixture was stirred at 0° C. for 1 hr. and at room temperature for 3 days. Saturated aqueous sodium bicarbonate (250 mL) was added and the aqueous solution was washed with methylene chloride (3×500 mL). The combined organic layers were washed with 500 mL saturated aqueous sodium chloride, dried (magnesium sulfate), filtered, and concentrated to afford 20.6 of the title compound of Step B.

Provenance & Evidence