(7s,8r)-Ethyl 8-((r)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt → (7S,8R)-ethyl 8-amino-1,4-dioxaspiro[4.5]decane-7-carboxylate 4-methylbenzenesulfonate

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Reaction Steps

10% Pd/C (Degussa, 50% wet, 1.0 g, 9.40 mmol) was carefully wetted down under argon with ethanol, and then (7S,8R)-ethyl 8-((R)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt (10.3 g, 20.37 mmol) in ethanol (75 mL) was added. The mixture was then hydrogenated on a Parr Shaker apparatus for about 16 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give (7S,8R)-ethyl 8-amino-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt (8.10 g, 20.18 mmol, 99% yield) as a tacky white glass. MS (ESI+)=230.12 (M+H)+.

Provenance & Evidence