Ethane, 2-bromo-1,1-diethoxy- → (2S)-2-(2',2'-Diethyloxyethylamino)-3-phenylpropionic Acid Ethyl Ester

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A solution of L-phenylalanine ethyl ester (8.37 g, 46.8 mmol, 1 equiv), bromoacetaldehyde diethyl acetal (10.6 mL, 70.1 mmol, 1.5 equiv), and DIEA (16.2 mL, 93.4 mmol, 2.0 equiv) in DMF (100 mL) was heated at 80° C. for 2 d. The resulting solution was cooled to 23° C., taken up in chloroform (200 mL), washed with 10% aqueous potassium carbonate (3×50 mL), dried over potassium carbonate, and concentrated. Purification of the residue by silica gel chromatography yield 7.4 g (54%) of product. 1H NMR (CDCl3) δ 1.13-1.23 (m, 9H), 2.61 (dd, 1H, J=11.8, 5.9), 2.78 (dd, 1H, J=11.8, 5.9), 2.96-3.03 (m, 2H), 3.46-3.53 (m, 1H), 3.55-3.70 (m, 4H), 4.18 (q, 2H, J=7.1), 4.57 (t, 1H, J=5.5), 7.19-7.33 (m, 5H).

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