HCID 59536616, compound → (S)-3-((S)-1-(6-methoxy-2-methyl-3-pyridyloxy)-3-methylbutyl)-pyrrolidine

Participants

Reaction Conditions

Reaction Steps

Charge a 400 mL stainless steel autoclave with 20% by weight Pd/C (10%, wet, 820 mg) followed by a solution of (S)-1-benzyl-3-((S)-1-(6-methoxy-2-methyl-3-pyridyloxy)-3-methylbutyl)-pyrrolidine (4.1 g, 11.126 mmoles) in ethanol (82 mL). Purge with H2 gas (3×50 PSI), then charge the vessel with H2 gas (50 PSI). Heat the reaction mixture to 60° C.1 and stir at 60° C. for 24 hours. The pressure of the vessel increases to ˜55 PSI at 60° C. and the vessel is refilled with H2 gas as needed. Allow the reaction mixture to cool to room temperature, filter through a medium fritted funnel charged with celite (wet with ethanol), and wash with ethanol (˜80 mL). Concentrate under reduced pressure to give (S)-3-((S)-1-(6-methoxy-2-methyl-3-pyridyloxy)-3-methylbutyl)-pyrrolidine as a light yellow oil (3.02 g, 10.848 mmoles, 97.5% yield). 1H NMR (300 MHz, CDCl3) δ 7.12 (d, 1H, J=8.79 Hz), 6.50 (d, 1H, 8.79 Hz), 4.2 (aq, 1H, Ja=7.03 Hz, Jb=5.27 Hz), 3.87 (s, 3H), 3.08-2.94 (m, 2H), 2.94-2.82 (m, 1H), 2.82-2.70 (m, 1H), 2.50-2.26 (m, 3H), 2.36 (s, 3H), 1.94-1.78 (m, 1H), 1.78-1.52 (m, 3H), 1.44-1.30 (m, 1H), 0.898 (at, 6H, Ja=6.45 Hz, Jb=7.03 Hz). LC/MS=279.3 (M+1).

Provenance & Evidence