2-Amino-1,3-propanediol (20.1 g, 220 mmol) was added to a solution of tetra-o- benzyl-5-oxo-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanemethanol (35.0 g, 63.4 mmol) in methanol (350 mmol) at room temperature and stirred for 60 minutes. Sodium cyanoborohydride (14 g, 222 mmol) was added and the pH was adjusted to 8.0 with concentrated hydrochloric acid and stirred for 25-30 hours. Water was added to the reaction mixture product, extracted with ethyl acetate and partitioned, the ethyl acetate layer was dried with anhydrous sodium sulfate and concentrated to obtain 38.6 g of a pale yellow oily product. The purity of the product was 90.0% as measured by high performance liquid chromatography (HPLC).
