Triethylamine → HCID 86606385, Verbindung

To a solution of D-serine methyl ester hydrochloride (0.91 g) in ethanol (18 mL) was added 7-oxoheptanenitrile (0.67 g) and triethylamine (0.6 mL) (see: Kubodera, N. et al, Heterocycles 1982, 19, 1285) and the mixture was stirred under N2 for 1 h. To the solution was then added Na(CN)BH3 (0.4 g) and the resultant cloudy suspension was further stirred under N2 for 1 h. The mixture was quenched with water and concentrated in vacuo and the residue diluted with ethyl acetate/saturated NaHCO3. The organic layer was separated and the aqueous layer extracted with ethyl acetate (3×). The organic layers were washed with water, brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography. Eluting with 5–10% (v) methanol in dichloromethane gave the desired product 2-1 (620 mg). 1H NMR (400 MHz, CDCl3): δ 3.78 (m, 1H), 3.77 (s, 3H), 3.59 (dd, 1H), 3.38 (dd, 1H), 2.72 (m, 1H), 2.53 (m, 1H), 2.36 (t, 2H), 1.70 (m, 2H), 1.55–1.35 (m, 6H).

1. customThe mixture was quenched with water
2. concentrationconcentrated in vacuo
3. additionthe residue diluted with ethyl acetate/saturated NaHCO3
4. customThe organic layer was separated
5. extractionthe aqueous layer extracted with ethyl acetate (3×)
6. washThe organic layers were washed with water, brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated
10. customthe residue was purified by chromatography
11. washEluting with 5–10% (v) methanol in dichloromethane

ORD-Eintrag

ord-78ae0bb53d85454e8582024dfe36454d

Quelldatensatz

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07109223B2