Methyl morpholine oxide → HCID 71285294, compound

Participants

Reaction Conditions

Reaction Steps

To activated 4 Å molecular sieves (4.3 g, 250 mg/mmol) was added a solution of 1-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-ol obtained above (ca. 17.22 mmol) in DCM (90 mL). The mixture was cooled to 0° C. before NMO (3.00 g, 25.61 mmol) and TPAP (300 mg, 0.85 mmol, 5 mol %) were added subsequently. The reaction was stirred at 0° C. for 15 min and then allowed to warm to room temperature. After 2 h complete conversion of staring material was observed. Molecular sieves were filtered off and were washed with DCM. The mother liquor was concentrated and the residue was purified by column chromatography (EtOAc/hexanes, 5-15% gradient). 1-(4-(Benzyloxy)-1-methyl-1H-indol-5-yl)butan-1-one was obtained as a white solid (4.85 g) in 92% yield over 2 steps.

Provenance & Evidence