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13th April 2011 @ 08:07
Repetition of the racemization experiments on enantioenrichend (S)-(+)-PZQamine with Rhodium on charcoal to verify the results

Scheme MW50-8.png


See also:
Racemization of S-(+)-PZQamine with Pd/C (MW50-1 to MW50-3)
Racemization of S-(+)-PZQamine with Pd/C (MW50-4)
Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)
Thiyl radical-mediated racemization of S-(+)-PZQamine (MW50-8)
Racemization of S-(+)-PZQamine (MW50-9) and (R) -(-)-PZQ (MW55-5) with sodium naphthalide
Repetition: Racemization of S-(+)-PZQamine (MW50-10) and R -(-)-PZQ (MW55-6) with sodium naphthalide
Racemization of S-(+)-PZQamine with Raney Nickel under high pressure and high temperature (MW50-11)

Hazard and Risk Assessment:
HRAF MW50.pdf


Start time: 5:30 PM 13/04/2011
End time: 9:30 AM 15/04/2011

To a solution of enantioenrichend (S)-PZQamine (50 mg, 247 µmol, MW: 202.3 g/mol) in toluene (2 mL) was added Rhodium on Charcoal (50.9 mg, 49.4 µmol, 0.2 eq.; 10% Rh on C, M.W. (Rh) 102.9 g/mol) and heated to 100°C for 39 h.

TLC:

- column (silica gel; ethyl acetat, 100% then ethyl acetate, methanol, triethylamine, 10:1:0.1)
PZQamine: 13.2 mg (26%)
[α]D20 = +161° (c=1, DCM)
Data: 1H NMR MW50-13 fr_2.pdf

unpolar 'side product': 23.9 mg
Rf=0.45 (ethyl acetate, stain: potassium permanganate)
[α]D20 = +90° (c=1, DCM)
1H NMR: Data: 1H NMR MW50-13 fr_1.pdf
Attached Files
1H NMR MW50-13 fr_1.pdf
1H NMR MW50-13 fr_2.pdf