Acetic Acid → (S)-methyl 2-((4-methoxybenzyl)amino)-2-phenylacetate

Temperatur

0 °C

To a solution of (S)-methyl 2-amino-2-phenylacetate (1.0 g, 6.06 mmol) in anhydrous MeOH (20 mL) was added 4-methoxy benzaldehyde (0.82 g, 6.06 mmol) and few drops of HOAc. After 30 min, the reaction mixture was cooled to 0° C., NaBH4 (0.69 g, 12.12 mmol) was added and the contents were stirred at ambient temperature. After 2 h, the reaction was quenched with ice cold H2O (10 mL), MeOH was removed under reduced pressure and the organic contents were extracted with EtOAc (3×25 mL). The combined organic extracts were washed with brine (1×20 mL), dried over Na2SO4, concentrated and the residue thus obtained was taken directly for step 2. MS ES+APCI calc'd. for C17H19NO3 [M+H]+ 286. Found 286.

1. waitAfter 2 h
2. customthe reaction was quenched with ice cold H2O (10 mL), MeOH
3. customwas removed under reduced pressure
4. extractionthe organic contents were extracted with EtOAc (3×25 mL)
5. washThe combined organic extracts were washed with brine (1×20 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customthe residue thus obtained

ORD-Eintrag

ord-a8f858f06830434ea26f9db2d0852543

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09233979B2