4-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyran → 1-[4-(benzylthio)tetrahydro-2H-pyran-4-yl]methanamine

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Reaction Steps

A solution of 4-benzylthio-2,3,5,6-tetrahydro-4-nitromethyl-4H-pyran (8 g) in dry ether (25 cm3) was added dropwise over a period of about 45 min to a stirred suspension of lithium aluminium hydride (3.8 g) in dry ether (200 cm3), cooled in an ice bath. When the addition was complete the mixture was heated under reflux for an additional hour. Excess lithium aluminum was destroyed by the careful addition of water, and then an aqueous solution of sodium potassium tartrate (200 cm3, 20% w/w) was added. The mixture was stirred until the solids had dissolved and the ether layer was then separated. The aqueous solution was then extracted with ether and the combined extracts then dried (MgSO4). Removal of the ether under reduced pressure gave the crude product which was purified via the recrystallisation of its hydrochloride salt using isopropanol. The purified amine (3.95 g, 59%) was obtained as a colourless liquid.

Provenance & Evidence