8-(2-azido-1-hydroxyethyl)-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one synthesis

Yield:1179336-42-5 80%

Reaction Conditions:

with sodium tetrahydroborate;ethanol at 20; for 1.5 h;

Steps:

Intermediate 17 8-(2-Azido-1-hydroxy-ethyl)-5-benzyloxy-4H-benzo[1,4]oxazin-3-one; A suspension of 8-(2-azido-acetyl)-5-benzyloxy-4H-benzo[1 ,4]oxazin-3- one (2 g, 5.91 mmol) in EtOH (80 mL) was treated with sodium borohydride (224 mg, 5.91 mmol) and the resultant mixture stirred at 20 ⁰C for 1.5 h. The mixture was partitioned between EtOAc and brine, the organic layer was dried, filtered and the solvent removed in vacuo. The crude solid was triturated with acetone (20 mL) to yield the title compound as a white solid. Yield: 1.60 g (80%).

References:

WO2010/15792,2010,A1 Location in patent:Page/Page column 51