Formic Acid → (R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamide

Temperature

0 °C

(R)-1-[4-(Benzyloxy)-3-nitrophenyl]-2-bromoethanol (0.2 g, 5.7 mmol) in THF:toluene (1:1, 5 mL) was reacted with PtO2 (1% w/w) on a Parr shaker at 45 psi at rt overnight. The next morning the PtO2 was removed by filtration over celite. The filtered solution was cooled to 0° C. and a solution of acetic anhydride (0.161 mL, 0.569 mmol) and formic acid (0.043 mL, 1.140 mmol) was added dropwise to a mixing solution of the aniline. The reaction was allowed to proceed at 0° C. for 30 min then warmed to rt and reacted for another 2 h. The reaction mixture was concentrated to near dryness then water was added. The aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were washed with NaHCO3, brine, dried over Na2SO4 (s), and concentrated to give a residue. Chromatography (1:1 Hexanes/EtOAc) gives the title compound (156 mg, 78% 2 steps). ES/MS calcd. C16H17BrNO3+350.0. found m/z=350 (M+H)+.

1. customThe next morning the PtO2 was removed by filtration over celite
2. temperaturethen warmed to rt
3. customreacted for another 2 h
4. concentrationThe reaction mixture was concentrated
5. additionwater was added
6. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
7. washThe combined organic layers were washed with NaHCO3, brine
8. dry with materialdried over Na2SO4 (s)
9. concentrationconcentrated
10. customto give a residue

ORD record

ord-0b3e45062f0541ef95dd2c1dc51e3449

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367829B2