N-Boc-L-alpha-phenylglycinol is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dye fields. Phenylglycinol-derived oxazolopiperidone lactams is used as starting materials for the enantioselective synthesis of piperidine-containing alkaloids.
GENERAL STEPS: Di-tert-butyl dicarbonate (31.82 g, 146.8 mmol) was slowly added to a solution of anhydrous tetrahydrofuran (292 mL) containing (R)-(-)-2-phenylglycinol (20.00 g, 145.8 mmol) and triethylamine (24.4 mL, 175.0 mmol) at 0 °C. The reaction mixture was stirred continuously for 3 hours at 0 °C. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure by rotary evaporator. The concentrated residue was dissolved in dichloromethane (200 mL) and washed with 1N hydrochloric acid (240 mL). The aqueous layer was back-extracted with dichloromethane (2 x 100 mL). All organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated again by rotary evaporator under reduced pressure to give a white solid product ((R)-tert-butyl 2-hydroxy-1-phenylethyl)carbamate (34.59 g, yield >99%). The product was characterized by 1H NMR (CDCl3): δ 1.43 (s, 9H), 2.29 (br s, 1H), 3.84-3.87 (m, 2H), 4.79 (br s, 1H), 7.29-7.39 (m, 5H).
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