in the equatorial position (hence indistinguishable from the label at C-2 of l), the deuterium at C-2 of 3 is axial and easily quantifiable. The 2: l ratio for Cl/C-2, proves that the hydroxyl epimerization results from ketone reduction by lithium aluminum deuteride. These results suggest that caution should be observed before using epoxide opening by lithium aluminum deuteride as a means of incorporating a stereospecific isotopic label in a cyclic system.
![N-[3-(4-aminobutylamino)propyl]acetamide Structure](https://image.chemsrc.com/caspic/269/14278-49-0.png)
