Reacción #320523

Ecuación de reacción

methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate

aluminum isopropoxide

→

methyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxy-propyl)-carbamate

Rendimiento 89.0%

Disolventes

isopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónhydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml
2. 2
   workup.ADDITIONdiluted with 125 ml of water
3. 3
   Temperaturacooled to 0° C.
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe residue was washed with water/isopropanol (4:1)
6. 6
   Otrodried

Procedimiento

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): 3323s, br. (NH, OH), 1689 (C=O), 1546s (amide II).

Fuente