The Journal of Organic Chemistry
Article
atmosphere, were added methoxymethoxybenzene (138 mg, 1.0
mmol) and THF (5 mL). The mixture was cooled to 0 °C, and to
it was added n-BuLi (1.2 equiv, 0.75 mL), dropwise via syringe as a 1.6
M solution in hexanes. The mixture was stirred for 1 h at 0 °C, and
then to it was added B(OiPr)3 (1.5 equiv, 0.35 mL). The ice−water
bath was removed and the mixture allowed to warm to room
temperature. A freshly prepared solution of HSA (1.5 equiv, 170 mg)
in 1 M aqueous NaOH (5 mL) was added and the resulting biphasic
mixture stirred for 16 h at room temperature. The reaction mixture
was diluted with H2O and extracted with EtOAc (2 × 30 mL). The
combined organic extracts were dried (Na2SO4) and concentrated in
vacuo. The residue was purified by flash chromatography (EtOAc/
hexanes) to afford the amine product (2ah: 142 mg, 93%), which had
1H and 13C NMR data that matched with that reported in the
literature.
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ASSOCIATED CONTENT
■
S
* Supporting Information
Complete characterization data including H and 13C NMR
1
spectra. This material is available free of charge via the Internet
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Acknowledgment is made to the Donors of the American
Chemical Society Petroleum Research Fund for support of this
research (Undergraduate Research Grant 52231-UR1, J.A.M.).
We thank NSERC (Discovery Grant, J.W.H.) and the
University of Winnipeg for further financial support, and
Westgrid and Compute Canada for supercomputing resources.
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