tert-Butyl (S)-((4-benzylmorpholin-2-yl)methyl)carbamate → (R)-2-N-Boc-aminomethylmorpholine

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl {[(2S)-4-(phenylmethyl)-2-morpholinyl]methyl}carbamate (4.9 g, 16 mmol) in ethanol (160 mL) was added 10% Pd/C (1.5 μg). The suspension was hydrogenated at 50 psi for 8 h. The reaction was filtered through a pad of Celite® and the pad was washed several times with methanol. The filtrate was concentrated to afford the title compound (3.35 g, 97%) as a colorless solid which was not purified further: LC/MS (ES) m/e 217 (M+H)+. The absolute stereochemistry of the title compound was determined by vibrational circular dichroism (VCD).

Provenance & Evidence