Aluminum isopropoxide → Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

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Reaction Conditions

Reaction Steps

25.57 g of methyl(S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate were added portionwise at 22° C. to a suspension of 21.44 g of aluminum isopropoxide in 260 ml of isopropanol. The suspension was stirred at 50° C./400 mbar for 2 hours, hydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml, diluted with 125 ml of water, cooled to 0° C. and filtered. The residue was washed with water/isopropanol (4:1) and dried, there being obtained 13.01 g (89%) of isomerically-pure methyl(1S,2S)-(1-benzyl-3-chloro-2-hydroxy-propyl)-carbamate, m.p. 162°-163.5° C. IR (KBr): 3323 s, br. (NH, OH), 1689(C=O), 1546 s (amide II).

Provenance & Evidence