Hydrochloric Acid → HCID 15623660, compound

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Reaction Steps

First, 0.1 g of lipoprotein lipase (LPL Amano 3, derived from a Pseudomonas strain and available from Amano Seiyaku, Inc.) and 10 g of the racemate (RS)-N-benzyl-3-butyryloxypyrrolidine were added to 100 ml of 0.1 M phosphate buffer solution (pH 7.0). After adjustment of the mixture to pH 7.0 by the addition of HCl, this mixture was allowed to react at 40° C. with agitation for 28 hours. The reaction mixture was extracted three times with 100-ml portions of hexane, and the solvent was removed from the extract under reduced pressure to yield 4.95 g of (S)-N-benzyl-3-butyryloxypyrrolidine in oily form. The residue remaining after the above hexane extraction was adjusted to pH 13 by the addition of NaOH, and then extracted three times with 100-ml portions of hexane. The solvent was removed from the extract under reduced pressure to yield 3.42 g of (R)-N-benzyl-3-hydroxypyrrolidine in oil form. The (S)-N-benzyl-3-butyryloxypyrrolidine obtained as described above was treated by vacuum distillation at 132°-137 ° C./3 mm Hg to yield 4.5 g of a colorless, transparent, purified product. The specific rotation of this product was [a]D20 -19.2° (c=5, MeOH). The NMR and IR spectra of this product coincided with those of the reference sample, and the results obtained by elemental analysis agreed with the calculated values.

Provenance & Evidence