Reaction #1688907

Reaction equation

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

hydrochloric acid

water

→

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

Yield 90.3%

Solvents

ethanol

Conditions

Workup

1. 1
   ConcentrationThe suspension was concentrated to 370 ml
2. 2
   Filtrationfiltered
3. 3
   Washthe residue was washed with water/ethanol (4:1)
4. 4
   Otherdried

Procedure

33.06 g of lithium aluminum tri-tert.-butoxyhydride were added portionwise at -15° C. to a suspension of 25.57 g of methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate in 280 ml of ethanol and the mixture was subsequently hydrolyzed at 0° C. with 140 ml of 3N hydrochloric acid and 170 ml of water. The suspension was concentrated to 370 ml, filtered and the residue was washed with water/ethanol (4:1) and dried, there being obtained 23.27 g (90%) of isomerically-pure methyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxy-propyl)-carbamate, m.p. 163°-164.5° C. IR (KBr): 3323s, br. (NH, OH), 1689 (C=O), 1546s (amide II).

Source