2,4,6-Trimethylpyridine → (3R,4R)-1-benzyloxycarbonyl-3-methanesulfonyloxy-4-methanesulfonyloxymethylpyrrolidine

Participants

Reaction Steps

Process C: (3R,4R)-[1-Benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol (150 mg) was dissolved in dichloromethane (12 mL) and 2,4,6-collidine (0.79 mL) was added to the solution. While this mixture was chilled in an ice water bath, methanesulfonyl chloride (46.2 μL) was added dropwise. The mixture was stirred for 2 hours in the ice water bath and was stored in a refrigerator (3° C.) for 15 hours. Subsequently, the reaction mixture was washed sequentially with water (2 mL), 1 mol/L hydrochloric acid (2×2 mL) and saturated brine (2×2 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane:ethyl acetate 1:2->ethyl acetate) to give 38.7 mg of (3R,4R)-1-benzyloxycarbonyl-3-methanesulfonyloxy-4-methanesulfonyloxymethylpyrrolidine as a pale yellow syrup and (3R,4R)-1-benzyloxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (133 mg) as a white syrup.

Provenance & Evidence