Reaction #577249

Reaction equation

lithium hydroxide

N-[3-(4-benzyloxy-phenyl)-1,1-bis-hydroxymethyl-propyl]-acetamide

methanol

water

→

2-Amino-2-[2-(4-benzyloxy-phenyl)-ethyl]-propane-1,3-diol

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate (500 ml)
2. 2
   Washwashed with brine (2×300 ml)
3. 3
   Dryingthe combined organic layers are then dried with Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under vacuum

Procedure

To a solution of crude N-[3-(4-benzyloxy-phenyl)-1,1-bis-hydroxymethyl-propyl]-acetamide in a mixture of tetrahydrofuran, methanol, water (1/2/2) (450 ml/900 ml/900 ml) is added at room temperature lithium hydroxide (32.7 g, 1.36 mol, 8.0 eq). The reaction mixture is stirred at 55° C. for 5 hours, then extracted with ethyl acetate (500 ml) and washed with brine (2×300 ml), the combined organic layers are then dried with Na2SO4, filtered and concentrated under vacuum. 2-Amino-2-[2-(4-benzyloxy-phenyl)-ethyl]-propane-1,3-diol is isolated after crystallization using ethyl acetate (28.8 g, 97%).

Source