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Supplementary data
Supplementary data associated with this article can be
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References and notes
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9. A typical procedure for hydrogenation: To a 460 ml
hastelloy bomb is added 10% Pt–C (2.2 g) and EtOH
(30 mL). The contents are agitated and pressurized under
hydrogen (95 psi) for 1 h. To the vessel is then added
concentrated HCl (20.8 g, 4 equiv) and 1a (20 g), as a
solution in EtOH (170 mL). The contents are repressurized
and agitated (500 rpm) until the starting material disap-
pears. The reaction mix is filtered over Celite and the pad
washed with 2 · 20 mL EtOH. The filtrate is then concen-
trated under vacuum at 40 ꢁC while EtOH (310 mL) is
added to compensate for volume loss. Distillation continues
until the final mass is ꢀ80 g. MTBE (120 mL) is then added
over 10 min at 40 ꢁC to facilitate crystallization of 2. After
cooling to room temperature, the slurry is agitated for 1 h,
filtered over a Buchner funnel, and the cake was washed
with 2 · 20 mL MTBE. After being pulled dry, the crude
weight is 11.65 g (76.2% yield).
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