HCID 67166124, compound → HCID 67164705, compound

Participants

Reaction Steps

(2-Methoxy-benzyl)-{3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzyl}-carbamic acid tert-butyl ester (51 g) was dissolved in a mixture of THF (250 mL), AcOH (225 mL) and water (150 mL) and the resulting mixture refluxed for a total of 10 hours. The majority of the tetrahydrofuran and acetic acid was evaporated and the pH of was adjusted to 8 using saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate (3×250 mL) and the combined organics were washed with water (250 mL), brine (250 mL), dried over sodium sulfate, filtered and evaporated. The crude material was purified in two portions by column chromatography eluting with dichloromethane:ethyl acetate (95:5 to 80:20 gradient) to give a yellow oil (total of 17.2 g).

Provenance & Evidence