(S)-6-(2-Methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one → (S)-6-Isobutyl-3-{1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

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Reaction Steps

A mixture of (S)-6-(2-methyl-allyl)-3-{(S)-1-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (48 mg; isomeric mixture from Intermediate X) and palladium on carbon (10 mg) in tetrahydrofuran (10 mL) was shaken in hydrogen atmosphere (50 psi) at room temperature for 6 h. Then, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1->95:5) to afford the title compound as a colorless resin-like solid.

Provenance & Evidence