Sodium Hydroxide → tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

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Reaction Steps

A solution of 1,1-dimethylethyl 2-{[(phenylcarbonyl)oxy]methyl}-4-morpholinecarboxylate (enantiomer E2) (1.08 g, 3.36 mmol) in methanol (30 mL) with 6N NaOH (5.6 mL. 33.6 mmol) was stirred at room temperature for 2 h. The methanol was removed under reduced pressure and the resulting mixture was partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over sodium sulfate and solvent removed under reduced pressure to give the desired compound. 1H NMR (400 MHz, DMSO-d6) d ppm 1.41 (s, 50H) 3.25-3.37 (m, 22H) 3.39-3.46 (m, 7H) 3.70 (d, J=12.88 Hz, 6H) 3.76-3.88 (m, 10H) 4.78 (t, J=5.68 Hz, 5H)

Provenance & Evidence