Morpholine → HCID 58356368, compound

Participants

Reaction Steps

1,1-Dimethylethyl 5-formyl-1-(1-methylethyl)-1H-pyrazole-3-carboxylate (118 mg) was dissolved in anhydrous DCM (10 ml), morpholine (0.048 ml) was added and the mixture was stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (210 mg) was added and the mixture was stirred at RT for 18 h. Sodium bicarbonate solution (20 ml) and DCM (20 ml) were added and separated then the aqueous layer was re-extracted with DCM (2×20 ml) and separated by hydrophobic frit. The combined organic layers were concentrated in vacuo and the residue was purified by flash chromatography on silica gel (20 g silica) eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 20 mins to give the title compound (101 mg) as a white solid.

Provenance & Evidence