Ammonium Chloride → 3-Phenylmorpholin-4-ol

Activated MnO2 (0.65 g, 7.41 mmol) was added to a solution of N-hydroxymorpholine (0.25 g, 2.47 mmol) in dichloromethane (15 mL) at 0° C. and the mixture was stirred for 1 h. The reaction mixture was filtered through a pad of Celite™ and Na2SO4. The filtrate was added dropwise to a solution of phenylmagnesium chloride (2.0 M in tetrahydrofuran, 2.47 mL, 4.94 mmol) at −10° C. The reaction mixture was stirred at 0° C. for 0.5 h and then saturated aqueous ammonium chloride solution (15 mL) and dichloromethane (15 mL) were added. The aqueous phase was separated and extracted with dichloromethane (2×20 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The crude product was subjected to flash chromatography on SiO2 eluting with 25% diethyl ether in hexanes to give the title compound (0.045 g, 11%) as a white crystalline solid.

1. filtrationThe reaction mixture was filtered through a pad of Celite™ and Na2SO4
2. stirringThe reaction mixture was stirred at 0° C. for 0.5 h
3. customThe aqueous phase was separated
4. extractionextracted with dichloromethane (2×20 mL)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-51d765313af94c1ebf88d2052b78c01c

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08053432B2