Water → (2s,4r)-n-t-Butoxycarbonyl-4-t-butyldimethylsiloxy-2-(alpha-hydroxybenzyl)pyrrolidine

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Reaction Steps

2.0M Phenylmagnesium bromide-tetrahydrofuran solution (22.8 ml, 45.6 mmol) was added dropwise to a solution of (2S,4R)-N-t-butoxycarbonyl-4-(t-butyldimethylsiloxy)prolinal (10 g, 30.4 mmol) in tetrahydrofuran (200 ml) at -78° C. in a nitrogen stream over 15 minutes. This reaction solution was gradually warmed and stirred at room temperature for 3 hours. After addition of water, the reaction solution was concentrated in vacuo. The resulting residue was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting oily residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=4:1) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(α-hydroxybenzyl)pyrrolidine (12.0 g, yield: 96.8%) as a colorless oily substance.

Provenance & Evidence