Sodium Hydroxide → (S)-(-)-1-Benzyl-3-pyrrolidinol

Beteiligte Stoffe

Reaktionsschritte

A liquid medium having the composition given in Example 2 was prepared and distributed in 100-ml portions into twenty-five 500-ml Sakaguchi flasks and steam-sterilized at 120° C. for 20 minutes. The contents of each flask was aseptically inoculated with 2 ml of a fluid culture obtained by cultivating Micrococcus luteus IFO 13867 in the same manner as in Example 2, and shake-culture was carried out at 30° C. for 24 hours. Cells were harvested from the resultant culture fluids by centrifugation and suspended in 500 ml of 100 mM phosphate buffer (pH 6.5). To this suspension was added 5 g of N-benzyl-3-pyrrolidinone, and 10 g of glucose. The reaction was allowed to proceed at 30° C. with stirring for 24 hours, while the reaction mixture wag maintained at pH 6.5 with 6N aqueous sodium hydroxide solution. Thereafter, the reaction mixture was extracted with 2.5 L of ethyl acetate, and the aqueous layer was further extracted with 1 L of ethyl acetate. The organic layers were combined and dehydrated over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The residue was distilled to give 3 g of (S)-N-benzyl-3-pyrrolidinol. The yield was 60%, the optical purity was 99.8% ee, the boiling point was 132 to 137° C./3 mm Hg, and the optical rotation [α]D20 was −3.77° (CH3OH, c=5). 1H-NMR δ (CDCl3): 1.63-1.76 (1H, m), 2.09-2.21 (1H, m), 2.26-2.37 (1H, m), 2.51-2.64 (2H, m), 2.75-2.85 (1H, m), 3.38 (1H, brs), 3.61 (2H, s), 4.24-4.33 (1H, m), 7.19-7.37 (5H, m).

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