Benzyl Bromide → 2-Benzyl 4-(tert-butyl) morpholine-2,4-dicarboxylate

Temperature

80 °C

In a 500-mL round-bottom flask, the 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (5.0 g, 22 mmol) was dissolved in DMF (75 mL). Benzyl bromide (3.6 ml, 30 mmol) was added via syringe, followed by potassium carbonate (4.8 g, 35 mmol). The sides of the glass were rinsed down with dmf (25 mL), and an air condenser was affixed, and the reaction mixture was heated at 80° C. in an oil bath for 14 h. The reaction was cooled to ambient temperature and concentrated. The residue was transferred to a separatory funnel with 60% ether-hexane (300 mL), and the organic layer was extracted with water (75 mL), half-saturated brine (30 mL), and saturated brine (30 mL), then was dried over sodium sulfate and concentrated. The residue was purified through silica gel (500 mL) using 20% to 30% EtOAc-hexane to afford the title compound (6.81 g, 21 mmol). MS m/z 266 (M+1-isobutylene).

1. washThe sides of the glass were rinsed down with dmf (25 mL), and an air condenser
2. temperatureThe reaction was cooled to ambient temperature
3. concentrationconcentrated
4. customThe residue was transferred to a separatory funnel with 60% ether-hexane (300 mL)
5. extractionthe organic layer was extracted with water (75 mL), half-saturated brine (30 mL), and saturated brine (30 mL)
6. dry with materialwas dried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified through silica gel (500 mL)

ORD record

ord-eeced9fcf1c64aa3bdcf9b9e2ef6e6f5

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872009B2