HCID 86690246, compound → (3S,4S)-4-methoxy-3-methylpiperidine

Participants

Reaction Steps

To a solution of (3S,4S)-benzyl 4-methoxy-3-methylpiperidine-1-carboxylate (4.0 g, 15.19 mmol) in MeOH (150 mL) under an argon atmosphere was added wet Pd/C [(5% dry basis) (1.617 g, 0.759 mmol)] The atmosphere was replaced with hydrogen gas via a balloon. The heterogeneous mixture was stirred for 1 hour at room temperature, and then filtered through Celite®. The filter cake was washed with dichloromethane (150 mL) followed by 20% MeOH/DCM (150 mL). The eluent was concentrated to afford (3S,4S)-4-methoxy-3-methylpiperidine which was used without the need for further purification. 1H NMR (400 MHz, CD2Cl2) δ ppm 0.91 (d, J=6.6 Hz, 3 H) 1.20 (tdd, J=12.2, 12.2, 10.5, 4.3 Hz, 1 H) 1.37-1.55 (m, 1 H) 2.03 (ddt, J=12.6, 4.2, 3.0, 3.0 Hz, 1 H) 2.21 (dd, J=12.6, 10.6 Hz, 1 H) 2.53 (td, J=12.4, 2.8 Hz, 1 H) 2.70-2.81 (m, 1 H) 2.95 (ddd, J=12.5, 4.3, 1.6 Hz, 1 H) 3.01-3.11 (m, 1 H) 3.31 (s, 3 H).

Provenance & Evidence