Acetaldehyde → HCID 61695367, compound

To a suspension of glycine ethyl ester hydrochloride (3.0 g, 0.021 mol) in DCM (80 mL) was added Et3N (3.0 mL, 0.021 mol). The resulting mixture was stirred at room temperature for 10 minutes, then acetaldehyde (1.2 mL, 0.021 mol) was added, followed by the drop-wise addition of TMSCN (2.86 mL, 0.021 mol). The resulting homogeneous solution was stirred at room temperature for 18 hours, then was diluted with DCM (100 mL) and washed with brine (100 mL), dried (Na2SO4), and concentrated in vacuo. The crude mixture was purified by flash column chromatography on silica gel (7:3 EtOAc/hexane). The title compound (3.5 g, 87%) was isolated as its white, solid, hydrochloride salt. TLC Rf (free base) 0.8 (EtOAc). 1H NMR (methanol-d4) δ1.34 (t, J=7.2 Hz, 3H), 1.73 (d, J=7.2 Hz, 3H), 4.16 (d, J=4 Hz, 2H), 4.33 (q, J=7.2 Hz, 2H), 4.70 (q, J=7.2 Hz, 1H).

1. stirringThe resulting homogeneous solution was stirred at room temperature for 18 hours
2. washwashed with brine (100 mL)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customThe crude mixture was purified by flash column chromatography on silica gel (7:3 EtOAc/hexane)

ORD record

ord-a822c3c460fa46299819093699a10585

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506761B1