(E)-tert-butyl 4-methyl-4-((5-oxohex-3-en-1-yl)oxy)piperidine-1-carboxylate → Tert-butyl 4-methyl-4-((5-oxohexyl)oxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (E)-tert-butyl 4-methyl-4-((5-oxohex-3-en-1-yl)oxy)piperidine-1-carboxylate (6.2 g, 19.91 mmol) in MeOH (100 mL) was added 10% Pd/C (2.119 g, 1.991 mmol) and the flask was three times evacuated and released to H2, then left under balloon H2 atmosphere for 5 h. Then, filtered and concentrated to give tert-butyl 4-methyl-4-((5-oxohexyl)oxy)piperidine-1-carboxylate (5.8 g, 18.50 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 3.77-3.70 (m, 2H), 3.32 (t, J=6.3 Hz, 2H), 3.13 (t, J=11.2 Hz, 2H), 2.48 (t, J=7.3 Hz, 2H), 2.16 (s, 3H), 1.77-1.62 (m, 4H), 1.59-1.53 (m, 2H), 1.48 (s, 9H), 1.45-1.37 (m, 2H), 1.16 (s, 3H). LCMS (M+Na)=336.4.

Provenance & Evidence