Synthesis and 1H NMR spectroscopic studies of partially deuterated N-propionyl derivative of chiral auxiliary chiracamphox spiro-oxazolidin-2-one

Abstract EN

In order to distinguish between the prochiral methylene protons HA and HB in the N-propionyl derivative of the chiral auxiliary spiro-oxazolidin-2-one, the partially deuteration of one of these two protons was employed.

A new method was employed for synthesis of the N-propionate partially deuterated derivative using lithium di-isopropyl amide (LDA) to form lithium enolate which was treated with AcOD to yield non-isolated mixture of both the N-propionyl derivative and its partially deuterated derivative.

1H NMR studies of the product revealed that the partially deuteration was occurred and confirmed that the two diastereotopic protons HA and HB are distinguishable