Benzaldehyde → (R)-2-(Benzylamino)-3-hydroxypropanoic acid

Temperatur

0 °C

To a mixture of D-serine (25.0 g, 0.237 mol) and 200 mL anhydrous methanol was added sodium cyanoborohydride (11.95 g, 0.190 mol), while maintaining the temperature at 0° C. with an ice bath. Then, benzaldehyde (26.5 mL, 0.261 mol) was added to the reaction flask, dropwise, at 30° C. The mixture was stirred for 60 Hr. at room temperature. Then, the mixture was filtered and rinsed with methanol (50 mL). The white solid was dried in a vacuum oven at 40° C. and 10 mmHg over 2 nights: 24.5 g. The filtrate was retained and the solvent was evaporated. This oil was passed through a silica gel column (10% MeOH/CH2Cl2) and 3.4 g of the desired compound was isolated. The total amount of the product was 27.9 g (60.0% yield). 1H NMR (DMSO-d6) δ3.25 (m, 1H, CH), 3.85 (m, 2H, CH2), 4.11 (d, 2H, benzylic CH2), 7.45-7.53 (m, 5H, ArH).

1. customat 30° C
2. customat room temperature
3. filtrationThen, the mixture was filtered
4. washrinsed with methanol (50 mL)
5. customThe white solid was dried in a vacuum oven at 40° C.
6. wait10 mmHg over 2 nights
7. customthe solvent was evaporated

ORD-Eintrag

ord-c56e3c6712584ea59046da4379673638

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06750216B2