Tetrahydrofuran → HCID 60208244, compound

Temperature

0 °C

A 1000 mL round bottom flask was charged with benzyl (1R)-1-methyl-2-oxoethylcarbamate (59.4 mmol) and 347 mL of anhydrous methanol. The resulting mixture was cooled to 0° C. and glycine methyl ester hydrochloride (29.3 g, 237.6 mmol) was added. After 10 minutes, 1.0 M NaCNBH4 in THF (95 mL, 95.0 mmol) was added and the reaction was allowed to warm to 22° C. overnight. The reaction mixture was then concentrated, redissolved in diethyl ether (200 mL) and placed in a separatory funnel. The organic phase was washed with saturated NaHCO3 (200 mL) and separated. The basic aqueous layer was washed twice with diethyl ether (2×200 mL), and the combined organic layers were washed with brine (2×200 mL), dried with Na2SO4 and concentrated. Silica gel chromatography using 2:1 hexanes/ethyl acetate with gradual polarization to 1:1 hexanes/ethyl acetate provided the desired product as a clear oil in 75% yield (12.5 g, 44.6 mmol).

1. temperatureto warm to 22° C. overnight
2. concentrationThe reaction mixture was then concentrated
3. dissolutionredissolved in diethyl ether (200 mL)
4. customplaced in a separatory funnel
5. washThe organic phase was washed with saturated NaHCO3 (200 mL)
6. customseparated
7. washThe basic aqueous layer was washed twice with diethyl ether (2×200 mL)
8. washthe combined organic layers were washed with brine (2×200 mL)
9. dry with materialdried with Na2SO4
10. concentrationconcentrated

ORD record

ord-3a4686037d78448ba4929ff0f4d60fd0

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625909B2