Methyl benzilate → Hydroxy-diphenyl-acetic acid (S)-1-methyl-pyrrolidin-2-ylmethyl ester

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((S)-1-Methyl-pyrrolidin-2-yl)-methanol (2.38 ml, 20 mmol) and hydroxy-diphenyl-acetic acid methyl ester (7.27 g, 30 mmol) are suspended in toluene (20 ml). Molecular sieve 4A (3 g) is added and the suspension is heated under stirring to 80° C. Sodium (0.46 g, 20 mmol) is added and the reaction mixture stirred at 80° C. for 3 hours. The reaction mixture is cooled to room temperature, solid filtered off, and washed with toluene. The filtrate is washed once with saturated aqueous NaHCO3 solution (50 ml) and twice with aqueous HCl 1M (30 ml each). The combined acidic aqueous layers are adjusted to pH 8 with saturated aqueous NaHCO3 solution. The emulsion is extracted with ethyl acetate (50 ml). The combined ethyl acetate layers are dried over sodium sulphate, filtered off and evaporated to dryness to give the product as a yellow oil that crystallises on standing. (M+H)+:326.2

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