D
R. Kadyrov, O. L. Tok
PSP
Synthesis
(3R)-3-[(tert-Butoxycarbonyl)amino]azepane (3b)
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Prepared according to the general procedure, from 2b (22.8 g, 0.1
mol). An analytically pure sample was obtained by vacuum sublima-
tion.
Yield: 18.6 g (87%); colorless solid; mp 96–98 °C.
[]D22 +9.2 (c 1.0, CHCl3) [Lit.8 (3S): []D25 –12.1 (c 1.0, EtOH)].
1H NMR (601 MHz, CDCl3): = 4.98 (br s, 1 H), 3.65 (br s, 1 H), 2.92–
2.80 (m, 2 H), 2.78–2.67 (m, 2 H), 1.79–1.68 (m, 2 H), 1.65–1.50 (m, 4
H), 1.50–1.35 (m, 1 H), 1.34 (s, 9 H).
13C NMR (151 MHz, CDCl3): = 155.25, 78.79, 53.56 (CH2), 50.87 (CH),
49.34 (CH2), 34.31 (CH2), 30.31 (CH2), 28.44 (Me), 22.07 (CH2).
MS (EI): m/z (%) = 157 (11), 141 (14), 97 (100), 82 (32), 57 (71).
HRMS (ESI-TOF): m/z [M + H]+ calcd for C11H22N2O2: 215.1759; found:
215.1756.
Conflict of Interest
The authors declare no conflict of interest.
Acknowledgment
The authors thank Gudrun Welzel and Dr. Jens Holz of the Leibnitz In-
stitute for Catalysis for measuring optical rotations and Dr. Ralf
Jackstel for providing MS and HRMS spectra. We thank Dr. Jonathan
Bould of the Institute of Inorganic Chemistry, Academy of Sciences of
the Czech Republic for assistance with manuscript preparation.
Supporting Information
Supporting information for this article is available online at
details for 1a and 1b, determination of the enantiomeric excess of 3a
and 3b, and 1H and 13C NMR spectra of compounds.
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© 2021. Thieme. All rights reserved. Synthesis 2021, 53, A–E