Potassium Phosphate, Tribasic → tert-Butyl ((trans)-2-(4-cyclopropylphenyl)cyclopropyl)carbamate

Temperatur

100 °C

To a 30-mL microwave tube were added tert-butyl (trans-2-(4-bromophenyl)cyclopropyl)carbamate (400 mg, 1.281 mmol), cyclopropylboronic acid (143 mg, 1.666 mmol), potassium phosphate (952 mg, 4.48 mmol), tricyclohexylphosphine (35.9 mg, 0.128 mmol), toluene (4 mL) and water (0.2 mL), and the mixture was degassed by bubbling N2. Palladium(II) acetate (14.38 mg, 0.064 mmol) was added and the tube was sealed. The mixture was heated at 100° C. with stirring for 4 h. The mixture was cooled and quenched with water (5 mL) and extracted with EtOAc (3×). The extract was dried (Na2SO4) and concentrated. The residue was purified using column chromatography (silica gel, 0 to 70% EtOAc/hexanes) to give 267 mg of product as pale yellow solid. MS: (M+H)+=274.2. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.61-0.73 (m, 2H), 0.90-1.01 (m, 2H), 1.08-1.24 (m, 2H), 1.42-1.52 (s, 9H), 1.81-1.94 (m, 1H), 1.98-2.12 (m, 1H), 2.70 (br. s., 1H), 6.91-7.12 (m, 4H).

1. customthe mixture was degassed
2. customby bubbling N2
3. customthe tube was sealed
4. temperatureThe mixture was cooled
5. customquenched with water (5 mL)
6. extractionextracted with EtOAc (3×)
7. dry with materialThe extract was dried (Na2SO4)
8. concentrationconcentrated
9. customThe residue was purified

ORD-Eintrag

ord-87480e5d3c364ab2914a1d169757dc68

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853408B2