Hydrochloric Acid → HCID 15623660, compound

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.

1. customto react at 40° C. with agitation for 28 hours
2. extractionThe reaction mixture was extracted three times with 100-ml portions of hexane
3. customthe solvent was removed from the
4. extractionextract under reduced pressure

ORD record

ord-f9a8e70e99644786b1dd66f94b39984d

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05187094