Hydrochloric Acid → (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol

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Reaction Conditions

Reaction Steps

To a suitable reactor was added 4a (52.3 g, 162 mmol), MeOH (810 mL), and 25% NaOMe/MeOH (8.1 mmol) at 20-30° C. under N2. The mixture was stirred at 20-30° C. for 2 hr, and 1 N HCl aqueous solution (16.2 mmol) was added at this temperature. The separated organic portion was concentrated at 40-50° C. under reduced pressure. Toluene (1100 mL) was added and the mixture was heated to 108-110° C. for dissolution. The mixture was cooled to 45-50° C. and stirred for 30 min. The mixture was further cooled to 20-30° C. and stirred for 1 hr. The mixture was filtered, and the filtered cake was washed with toluene (220 mL). The wet cake was dried at 40-50° C. under reduced pressure to give diol 7 as an off-white to white powder (39.5 g, 87% yield).

Provenance & Evidence