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Helvetica Chimica Acta – Vol. 95 (2012)
MeOH (1 ml). Then NaBH4 (0.125 mmol, 5 mg) was added at 08, and the mixture was stirred for 1 h. The
resulting residue was purified by FC (hexanes/AcOEt 4 :1): pure (1S,2S)-2-methyl-1-(4-nitrophenyl)-
propane-1,3-diol (10) [23]: HPLC (Chiralpak AD, hexane/i-PrOH 96 :04, 0.9 ml/min; 254 nm): tR 72.965
(minor) and 74.885 (major). 1H-NMR (300 MHz): 0.78 (d, J ¼ 7.0, 3 H); 2.01 – 2.06 (m, 1 H); 2.74 (br. s,
1 H); 3.72 – 3.85 (m, 3 H); 4.72 (d, J ¼ 7.8, 1 H, ꢀantiꢁ), 7.54 (d, J ¼ 8.7, 2 H); 8.23 (d, J ¼ 8.7, 2 H).
13C-NMR: 13.6; 41.5; 67.4; 79.3; 123.6; 127.5; 147.4; 150.5.
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