Water → HCID 57554657, compound

Participants

Reaction Steps

Tert-butyl (1R,3S)-1-(hydroxymethyl)-3-(4-octylphenyl)cyclopentylcarbamate (3.9 g, 9.66 mmol) was dissolved in dichloromethane (193 ml) under nitrogen to give a colorless solution. Dess-Martin periodinane (4.51 g, 10.63 mmol) (Aldrich) was added and the reaction stirred for about 3 h. LC/MS showed the reaction was complete. Methylene chloride (100 mL) and water (100 mL) were added and the layers separated and extracted with methylene chloride (2×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to an off-white solid. The residue was purified by flash column chromatography (120 g Redi-Sep) eluting with ethyl acetate/heptane and the product fractions combined. Solvents were removed under reduced pressure to provide tert-butyl (1R,3S)-1-formyl-3-(4-octylphenyl)cyclopentylcarbamate (3.40 g, 88%) as an off white solid: LC/MS (method f) Rt=3.58 min.; MS m/z: 401.36 (M+H)+.

Provenance & Evidence