Reaction #347096

Reaction equation

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

aluminum isopropoxide

→

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

Yield 89.3%

Solvents

isopropanol

Conditions

Workup

1. 1
   Concentrationhydrolyzed 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
   Temperaturecooled to 0° C.
4. 4
   Filtrationfiltered
5. 5
   WashThe residue was washed with water/isopropanol (4:1)
6. 6
   Otherdried

Procedure

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, yielding 23.01 g (89%) of isomerically-pure methyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxypropyl)-carbamate, m.p. 162°-163.5° C. IR (KBr): 3323s, br. (NH, OH), 1689 (C=O), 1546s (amide II).

Source