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sodium sulfate. Aer removal of solvents, the obtained crude
was puried by chromatographic column (eluent: AcOEt). The
fractions corresponding to (R)- or (S)-2 were collected, affording
oils aer evaporation of the solvent, with yields of 73% and
71%, respectively. The NMR spectra of (ꢁ)-2,6 (R)-2 and (S)-2
were found identical.
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´
C. Binda, F. Hubalek, M. Li, Y. Herzig, J. Sterling,
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(R)- or (S)-7-(prop-2-ynyloxy)-6,7-di-hydro-5H-cyclopenta[b]
pyridine ((R)- or (S)-2). 1H-NMR (CDCl3, 400 MHz), d (ppm):
2.09–2.16 (1H, m, H6anti), 2.32–2.39 (1H, m, H6syn), 2.42 (1H, t, J
¼ 2.4 Hz, OCH2CCH), 2.77 (1H, ddd, J ¼ 13.3, 8.7, 4.6 Hz,
H5anti), 3.00–3.08 (1H, m, H5syn), 4.38 (1H, dd, J ¼ 15.6, 2.4 Hz,
OCHaHbCCH), 4.46 (1H, dd, J ¼ 15.7, 2.4 Hz, OCHaHbCCH) 4.98
(1H, dd, J ¼ 7.0, 3.7, H7), 7.10 (1H, dd, J ¼ 7.6, 4.9 Hz, H3), 7.51
(1H, dd, J ¼ 7.6, 0.6 Hz, H4), 8.39 (1H, d, J ¼ 4.9 Hz, H2); 13C-
NMR (CDCl3, 100 MHz), d (ppm): 28.8 (C5), 31.7 (C6), 57.4
(OCH2CCH), 75.1 (OCH2CCH), 81.1 (OCH2CCH), 81.8 (C7),
124.0 (C3), 1334.0 (C4), 138.2 (C4a), 148.9 (C2), 163.4 (C7a); ESI-
HRMS: calculated for [C11H11NO + H]+ 174.0919, obtained
174.0917; [a]2D0 (R)-2 ¼ ꢂ38 (c1, CHCl3); [a]2D0 (S)-2 ¼ +39 (c1,
CHCl3); 5. HPLC chiral analyses: both racemates 3 and 6 were
individually analyzed in order to determine the retention times
of the respective enantiomers. A 0.5 ml minꢂ1 ow of 90 : 10
hexane/isopropanol was used. It was veried that retention
times of (ꢁ)-3 and (ꢁ)-6 were perfectly coincident. Thus, for an
accurate evaluation, at the end of each enzymatic reaction
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acetates 6 prior to HPLC analyses. Retention times: (R)-3 ¼ (R)-6
20, 1–8.
´
¼ 15.9 min; (S)-3 ¼ (S)-6 ¼ 22.9 min.
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Acknowledgements
˜
ˆ
The work was funded by Fundaçao para a Ciencia e a Tecnologia
(FCT)/MEC and FEDER under Program PT2020 (project UID/
QUI/50006/2013). CADS, IESD and FRA also thank FCT for the
grants SFRH/BPD/80100/2011, SFRH/BD/93632/2013 and SFRH/
BD/45545/2008, respectively. We also thank Novo Nordisk,
Denmark, for the generous gis of CALB lipase.
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3427–3430.
15 B. Neises and W. Steglich, Angew. Chem., Int. Ed. Engl., 1978,
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