1,2-Dichloroethane → tert-Butyl [2-(morpholin-4-yl)-2-oxoethyl]carbamate

To a stirred solution of N-(tert-butoxycarbonyl)glycine (3.0 g, 17.1 mmol) in DMF (75 mL), N,N-diisopropylethylamine (14.9 mL, 85.5 mmol) was added, followed by EDC (3.6 g, 18.8 mmol) and HOBT (2.5 g, 18.8 mmol) at 0° C., under argon. The resulting mixture was stirred for 0.5 h after which time morpholine (3.0 mL, 34.2 mmol) was introduced in a dropwise manner. Upon complete addition, the reaction was warmed to ambient temperature, stirred overnight and concentrated. The resulting residue was diluted with EtOAc and saturated NaHCO3. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were dried (MgSO4), filtered and concentrated to give 2.3 g (55%) of (2-morpholin-4-yl-2-oxo-ethyl)-carbamic acid tert-butyl ester which was used without further purification.

1. additionwas introduced in a dropwise manner
2. additionUpon complete addition
3. concentrationconcentrated
4. additionThe resulting residue was diluted with EtOAc and saturated NaHCO3
5. customThe layers were separated
6. extractionthe aqueous phase was extracted with EtOAc
7. dry with materialThe combined organics were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-44f71313330d42eeb557bb4c03afbcc1

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878706B1