Acetonitrile → 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanamine

To a solution of 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarboxamide (2.3 g, 7.32 mmol) in acetonitrile (9 ml) and Water (9.00 ml) was added phenyliodine bis(trifluoroacetate) (4.73 g, 11.00 mmol) and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was slowly poured into sodium bicarnate sat. solution (˜45 ml) and extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with water, brine and concentrated to give crude product (3.4 g). The crude product was purified by column (biotage, 50 g) eluted with 0-5% DCM/Methanol (mixture of 500 ml methanol and 60 ml 2M NH4OH in methanol) to give product 1-(4-bromophenyl)-3,3-dimethoxycyclobutanamine (1.06 g), 1H NMR (500 MHz, CDCl3): 7.48 (d, 2H), 7.32 (d, 2H), 3.27 (d, 3H), 3.17 (d, 3H), 2.66 (d, 2H), 2.44 (d, 2H).

1. extractionextracted with ethyl acetate (3×30 ml)
2. washThe combined organic phase was washed with water, brine
3. concentrationconcentrated
4. customto give crude product (3.4 g)
5. customThe crude product was purified by column (biotage, 50 g)
6. washeluted with 0-5% DCM/Methanol (mixture of 500 ml methanol and 60 ml 2M NH4OH in methanol)

ORD-Eintrag

ord-0080b0cb144e45159da1b468f2549838

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09221838B2