Cesium carbonate → (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

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Reaction Steps

A mixture of [(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]methyl methanesulfonate (12) (5.0 g, 16 mmol), 3-methoxybenzenethiol (1.9 mL, 16 mmol), cesium carbonate (15.3 g, 47.2 mmol) in anhydrous CH3CN (200 mL) was prepared under N2. The mixture was heated to reflux and stirred for 18 h. The reaction mixture was filtered and the filtrate concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1) to yield (1R,2R,4aS,8aS)-1-{[(3-methoxyphenyl)sulfanyl]methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (13-1) (4.0 g, 71% yield) as a yellow oil.

Provenance & Evidence