Chloroacetyl chloride → (5R)-5-Phenylmorpholin-3-one

(R)-Phenylglycinol (0.20 g, 1.46 mmol) in dry THF (10 mL) was treated with triethylamine (0.18 g, 1.75 mmol) in one portion at 0°, under an atmosphere of nitrogen. Chloroacetylchloride (0.20 g, 1.75 mmol) was added dropwise over 15 minutes at 0°. The mixture was allowed to reach room temperature over 1 hour then quenched with water (5 mL) and EtOAc (5 mL). The organic layer was washed with brine (10 mL), dried (MgSO4) and evaporated in vacuo to a white solid. NMR shows the precursor to the product (non ring closed). The solid was dissolved in dry THF (5 mL) and 10M NaOH was added slowly at 0°. The suspension was allowed to reach room temperature over 1.5 hours. The suspension was diluted with water (10 mL) and EtOAc (10 mL) and the organic layer was further washed with water (10 mL), then dried (MgSO4) and evaporated in vacuo to a crude yellow solid, which was taken to the next step without any purification.

1. customthen quenched with water (5 mL) and EtOAc (5 mL)
2. washThe organic layer was washed with brine (10 mL)
3. dry with materialdried (MgSO4)
4. customevaporated in vacuo to a white solid
5. customto the product (non ring closed)
6. dissolutionThe solid was dissolved in dry THF (5 mL)
7. addition10M NaOH was added slowly at 0°
8. waitto reach room temperature over 1.5 hours
9. additionThe suspension was diluted with water (10 mL) and EtOAc (10 mL)
10. washthe organic layer was further washed with water (10 mL)
11. dry with materialdried (MgSO4)
12. customevaporated in vacuo to a crude yellow solid, which
13. customwas taken to the next step without any purification

ORD record

ord-b03c7cee636b4a57b05b0cd42ee03161

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323464B2