Benzaldehyde → (R)-Methyl 2-(benzylamino)-3-hydroxypropanoate

Temperature

0 °C

The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). m/z=210 [M+H]+

1. customThe title compound was prepared
2. temperatureThe reaction mixture was then warmed up
3. stirringThe resulting mixture was stirred at room temperature overnight
4. washthe resulting solution was washed with diethyl ether (50 ml)
5. additionby adding solid potassium carbonate
6. extractionextracted with diethyl ether (3×50 ml)
7. dry with materialThe combined organic extracts were dried (Na2SO4)
8. concentrationconcentrated under vacuum

ORD record

ord-968689046e6246b9ab4f7de2ed57f37e

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919491B2