Morpholine → HCID 58356406, compound

Participants

Reaction Steps

1,1-Dimethylethyl 3-formyl-1-(1-methylethyl)-1H-pyrazole-5-carboxylate (491 mg) was dissolved in anhydrous DCM (20 ml), morpholine (0.198 ml) was added and the mixture was stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (873 mg) was added and the mixture was stirred at RT for 18 h. Sodium bicarbonate solution (50 ml) and DCM (50 ml) were added and separated and the aqueous layer was re-extracted with DCM (2×50 ml) and separated by hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (50 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 30 mins to give the title compound (628 mg) as a colourless oil.

Provenance & Evidence