Dimethyl Sulfoxide → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

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Reaction Steps

Swern reagent was prepared at -60° C. by adding slowly DMSO (0.899 ml, 11.5 mmol, dissolved in 2 ml of CH2Cl2) to oxalylchloride (0.503 ml, 5.85 mmol) in 10 ml of CH2Cl2. 15 Minutes later, (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol (1.81 g, 5.31 mmol), dissolved in 7 ml of CH2Cl2, was slowly added. After 1/2 h, NEt3 (5.18 ml, 37.2 mmol) was added and the temperature allowed to reach -25° C. The reaction was quenched by pouring onto crashed ice/NH4Cl, extracted twice with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97/3) yielded 1.583 g of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde as isomerically pure, colorless oil.

Provenance & Evidence