1'-Benzylspiro[isochroman-1,4'-piperidine] → 3,4-Dihydrospiro[2-benzopyran-1,4'-piperidine]

Participants

Reaction Steps

A solution of 1′-benzyl-3,4-dihydrospiro[isochromene-1,4′-piperidine] (0.40 g, 1.3 mmol) in ethanol (15 ml) was purged with argon. After addition of the palladium catalyst (10% Pd on activated charcoal, 0.14 g) the reaction vessel was filled with hydrogen gas. The mixture was stirred for 18 h at room temperature. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (0.23 g) as white solid with a purity of approx. 88% as assessed by 1H-NMR (contaminated with 1′-ethyl-3,4-dihydrospiro[isochromene-1,4′-piperidine]). MS m/e: 204 (M+H+).

Provenance & Evidence