Sodium Azide → HCID 86592849, compound

Participants

Reaction Conditions

Reaction Steps

Add NaN3 (0.33 g, 5.1 mmol) to a solution of 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-5-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.87 g, 1.7 mmol) in DMF (20 mL). Heat 24 H at 60° C., cool to 0° C. and quench with water. Concentrate to dryness. Partition between 20% iPrOH/CHCl3 and water. Extract 3×CHCl3. Wash the combined organics 2× with brine, dry over Na2SO4, filter and concentrate to dryness to afford the title compound (0.67 g, 84%) as a white foam as a mixture of cis isomers. MS(IS) 473.2 (M+); TLC (50% EtOAc/hexanes) Rf=0.8.

Provenance & Evidence