Acetone → HCID 53735847, compound

Participants

Reaction Steps

6-Allyl-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (Compound 234, 0.087 g, 0.2 mmol) was dissolved in acetone (2 mL) and water (0.25 mL). N-Methylmorpholine oxide (0.068 g, 0.58 mmol) was added, followed by a 2.5% OsO4 solution in t-BuOH (0.14 mL). The mixture reaction was stirred at room temperature for 14 hours. Sodium pyrosulfate (0.3 g) in water (1 mL) was added with stirring, and the resultant solution was filtered through Celite and washed with ethanol (10 mL). The solvents were removed and the residue was purified by flash column chromatography (100% EtOAc) to afford Compound 235 (0.086 g, 89%, as a mixture of isomers). Rf=0.12 and 0.06 (2:1 EtOAc/hexanes).

Provenance & Evidence