Sodium borohydride → 2-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanol

Beteiligte Stoffe

Reaktionsschritte

Sodium borohydride (646 mg, 17.1 mmol) was added over a period of 10 minutes to an ice-cooled solution of the product from Step A (4.89 g, 15.0 mmol) in methanol (85 mL). The reaction mixture was allowed to warm to room temperature and continued to stir for an additional 2 hours. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with methylene chloride (3×). The combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-((3-bromobenzyl)(methyl)amino)-1-p-tolylethanol (4.58 g, 93%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ 7.45 (s, 1H), 7.40 (d, J=5.8 Hz, 1H), 7.25-7.13 (m, 6H), 4.72 (dd, J=10.0, 3.7 Hz, 1H), 3.86 (br s, 1H), 3.68 (d, J=13.4 Hz, 1H), 3.49 (d, J=13.2 Hz, 1H), 2.62-2.47 (m, 2H), 2.33 (s, 3H), 2.30 (s, 3H).

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