Ethanol → Tert-butyl 5-(6-hydroxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

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Reaction Steps

[5-(6-Benzyloxy-naphthalen-2-yl)-2,2-dimethyl-1,3-dioxinan-5-yl]-carbamic acid tert-butyl ester (1.19 g, 0.00257 mol) and 20% Pd(OH)2 on carbon (20:80, palladium hydroxide:carbon black, 0.243 g; Aldrich) was suspended in ethanol (200 mL, 3 mol; Fisher), purged with N2 then stirred under H2 (balloon) at r.t. overnight. LCMS showed partial conversion. The mixture was transferred to a pressure vessel and continuously stirred under 50 psi of H2 for one day. The mixture was filtered, evaporated and dried in high vacuum to give a solid product (0.914 g, yield 95.3%).

Provenance & Evidence