Hydrochloric Acid → (S)-6-(Hydroxymethyl)morpholin-3-one

Participants

Reaction Steps

To a solution of t-BuOK (13.7 g, 122 mmol) in t-AmOH (175 mL) was added a solution of 2-chloro-N—[(S)-2,3-dihydroxypropyl]acetamide (8.1 g, 48.3 mmol) in t-AmOH (325 mL) at room temperature over 2 h. The resulting suspension was stirred for 1 h at room temperature. Methanol (50 mL) and water (5 mL) were added and the resulting solution was stirred for 0.5 h at room temperature before adjusting the pH to 5 by the addition of conc. HCl. The suspension was filtered and the solid washed with methanol. The filtrate was evaporated in vacuo, the resulting solid was slurried in methanol (50 mL) and filtered off to afford (S)-6-(hydroxymethyl)morpholin-3-one (1.3 g) as a white solid. A second crop was obtained by adding EtOAc (200 mL) to the filtrate and filtering the resulting solution through a silica plug (1×10 cm). The solvent was evaporated in vacuo to afford (S)-6-(hydroxymethyl)morpholin-3-one (3.9 g, overall yield 5.2 g, 82%) as a white solid.

Provenance & Evidence