Ethyl chloroacetate → (s)-5-Ethylmorpholin-3-one

To an ice cold, stirred suspension of NaH(60% in oil, 1.6 g, 39.0 mmol) in toluene (50 mL) was added dropwise a solution of (S)-2-aminobutan-1-ol (1.5 g, 17.0 mmol) in toluene (36 mL). After the addition was completed, the reaction mixture was warmed to room temperature and a solution of ethyl chloroacetate (2.3 g, 19.0 mmol) in toluene (9 mL) was added in a dropwise manner. The resulting mixture was then stirred at reflux for 20 h, cooled to room temperature, and solid NH4Cl (2.0 g, 38.7 mmol) was added to the reaction. The mixture was stirred for 20 min and then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 95:5 methylene chloride/CH3OH) to give (S)-5-ethylmorpholine-3-one (1.9 g, 88%) as an off-white semi-solid: 1H NMR and MS consistent.

1. additionAfter the addition
2. temperatureat reflux for 20 h
3. temperaturecooled to room temperature
4. stirringThe mixture was stirred for 20 min
5. concentrationconcentrated under reduced pressure
6. customThe crude material was purified by column chromatography (silica gel, 95:5 methylene chloride/CH3OH)

ORD 기록

ord-7dd76895fc6b4e01afe5033cd5406c1f

출처 데이터셋

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07863271B2