Hydrochloric Acid → 5-Hydroxymethyl-3-(2-methyl(ethyl)carbonylamino)pyrazole

Participants

Reaction Conditions

Reaction Steps

A solution of 787 mg of crude XII in 10 ml of dry THF was cooled to 0° C. in an ice bath. To this mixture was added 14 ml of 1 M LiAlH4 in THF while maintaining the temperature at 0° C. The reaction was allowed to stir at 0° C. for 6.5 hours at which point the solution was poured over 100 g of crushed ice. Once the ice had melted, the solution was brought to pH 7 by addition of HCl. The water layer was filtered to remove aluminum salts and the filtrate was extracted three times with 75 ml of ethyl acetate. The organic layer was collected, dried over MgSO4 and evaporated to an orange solid. The solid was purified on silica gel to give 79 mg of the alcohol (15%).

Provenance & Evidence