Diisopropylethylamine → Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

Beteiligte Stoffe

Reaktionsschritte

To a solution of (2R)-2-amino-2-phenylethanol (400 mg, 2.91 mmol) in CH2Cl2 (15 mL) was added BOC2O (636 mg, 2.91 mmol) and DIPEA (507 μL, 2.91 mmol). The reaction was stirred at room temperature for 18 hours, diluted with EtOAc (75 mL) and washed with H2O, brine, 1N HCl, brine, saturated NaHCO3, and brine (25 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography with 50% EtOAc/hexanes afforded tert-butyl [(1R)-2-hydroxy-1-phenylethyl]carbamate. Rf=0.23 (40% EtOAc/hexane). 1H NMR (CDCl3, 600 MHz) δ 7.27-7.37 (m, 5H), 5.27 (bs, 1H), 4.78 (bs, 1H), 3.83 (bs, 2H), 2.46 (bs, 1H), 1.44 (bs, 9H).

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