Sodium Hydroxide → (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

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Reaction Steps

A 0.976-g portion of the product obtained in Example 1, namely t-butyl [1(S)-benzyl-2(S)-hydroxy-3-chloropropyl]carbamate, was suspended in 8 ml of acetone, then 2 ml of 10% sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. The aqueous layer was separated and the organic layer was concentrated to dryness to give t-butyl [1(S)-benzyl-2(S),3-epoxypropyl]carbamate. After purification by preparative TLC, the optical purity (99.8% ee) was confirmed using a chiral column.

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