Isopropanol → N-(4-(Oxetan-3-YL)phenyl)acetamide

Temperatur

80 °C

(4-Acetamidophenyeboronic acid {670 mg, 3.7 mmol), Nickel (II) iodide (35 mg, 0.11 mmol), trans-2-aminocyclohexanol (17 mg, 0.11 mmol), and Sodium hexamethyldisilazane (690 mg, 3.7 mmol) were weighed into a microwave reaction vial. A septum was placed over the top, nitrogen was purged and Isopropyl alcohol (5.7 ml, 75 mmol) was added. The vial was purged with nitrogen for 10 minutes and 3-iodooxetane (344 mg, 1.87 mmol) was added in 0.75 ml isopropyl alcohol. The septum was replaced with a microwave vial cap and the mixture was heated in a microwave reactor (microwave conditions: CEM Discovery Explorer microwave reactor; Ramp time: 10 min; 80° C. for 30 min; power: 300 W). The crude reaction mixture was diluted with 8 ml EtOH and the suspension was filtered through a pad of solka Floc®. The pad was washed with 35 ml EtOH and the filtrate was concentrated. The crude material was purified by flash chromatography (SiO2, eluting with 40-60% EtOAc/CH2Cl2) to give the desired product as an oil (200 mg).

1. customwas purged
2. customThe vial was purged with nitrogen for 10 minutes
3. customvial cap
4. customThe crude reaction mixture
5. filtrationthe suspension was filtered through a pad of solka Floc®
6. washThe pad was washed with 35 ml EtOH
7. concentrationthe filtrate was concentrated
8. customThe crude material was purified by flash chromatography (SiO2, eluting with 40-60% EtOAc/CH2Cl2)

ORD-Eintrag

ord-5a49b4b067894506beb19446be3ed6fc

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09096634B2