Water → HCID 67165303, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzaldehyde (10 g) and 2-methoxybenzylamine (6 g) in toluene (150 mL) was added TsOH (100 mg). The mixture was heated at reflux in a Dean-Stark apparatus for a couple of hours. About 1 mL water was displaced. The reaction was checked by TLC, iso-hexane/EtOAc (4/1, Rf ˜0.5). The mixture was cooled and washed with aqueous bicarbornate, then concentrated in vacuo. The residue was azeotroped twice with toluene and was taken up in ethanol (150 ml). The solution was cooled to 0° C. and sodium borohydride (1.65 g) was added slowly. The reaction was left to warm to room temperature and was stirred overnight. Water was added (150 mL) and ethanol removed under vacuum. The residue was partitioned between aqueous bicarbonate and ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to give a yellow oil (6.5 g). The material was used in the next step without further purification.

Provenance & Evidence