反应详情

A suspension of glycine ethyl ester hydrochloride (10.0 g, 71.6 mmol) and NaBH3CN (5.00 g, 79.6 mmol) in MeOH (60 mL) was treated dropwise over 15 min with p-anisaldehyde (11.0 mL, 90.4 mmol). After stirring at room temperature overnight, the solvent was removed in vacuo. The residue was partitioned between CH2Cl2 (200 mL) and saturated aqueous NaHCO3 (300 mL). The aqueous layer was extracted with CH2Cl2 (2×200 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, hexanes/EtOAc, 90:10 to 50:50) gave the title compound (7.77 g, 49%) as a colorless liquid: MS (ESI) m/e 224 (M+H)+.

1. customthe solvent was removed in vacuo
2. customThe residue was partitioned between CH2Cl2 (200 mL) and saturated aqueous NaHCO3 (300 mL)
3. extractionThe aqueous layer was extracted with CH2Cl2 (2×200 mL)
4. washthe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customthe solvent was removed in vacuo
8. customPurification by flash column chromatography (silica gel, hexanes/EtOAc, 90:10 to 50:50)