Methyl morpholine oxide → (1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropanecarbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of the product of step A (5 g, 19.6 mmol), powdered 4 Å activated molecular sieves (10 g) and N-methylmorpholine oxide (3.5 g, 29.4 mmol) was stirred in DCM (100 mL) for 15 min at RT. Then the mixture was cooled to 0° C. and tetrapropylammonium perruthenate (0.69 g, 0.196 mmol) was added in one portion. The cold bath was removed and the mixture was stirred at RT for 1 h. The reaction was diluted with Et2O and stirred for 15 min at RT. The mixture was filtered through a plug of silica gel which was washed thoroughly with 2:1 hexane: ethyl acetate. The filtrate was concentrated to get a residue which was purified by column chromatography on silica (elution with 2:1 hexane:ethyl acetate) to yield the desired aldehyde. MS (ESI) m/z 260 [M+H]+.

Provenance & Evidence