ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-non-2-inoate → ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-nonanoate

Participants

Reaction Steps

A solution of 5.85 g of ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-non-2-inoate in 100 ml of tetrahydrofuran is hydrogenated in the presence of 1.2 g of platinum-on-charcoal (5% of Pt; a further 1.2 g of catalyst are added after 24 h) at room temperature under normal pressure for 33 h. Filtration of the reaction mixture over Hyflo® and concentration of the filtrate gives the crude title compound as a yellow oil: Rf (B)=0.32; FAB-MS: (M+H)+ =452.

Provenance & Evidence