Methyl iodide → HCID 71279463, compound

Temperature

0 °C

To a solution of 3-iodo-1,4,5,6,7,8-hexahydrocycloheptapyrazole (600 mg, 2.29 mmol) in THF (8 ml) at 0° C. was added KOt-Bu (360 mg, 3.2 mmol). The reaction mixture was stirred at 0° C. for 30 min then iodomethane (0.20 ml, 3.2 mmol) was added. Stirring was continued at 0° C. for 30 min then at room temperature for 2 h. The reaction was quenched with water and extracted with EtOAc (2×). The organics were dried over MgSO4 and concentrated. The residue was absorbed on SiO2 and chromatographed with 10% to 20% EtOAc/hexanes to afford 387 mg (61%) of 3-iodo-1-methyl-1,4,5,6,7,8-hexahydrocycloheptapyrazole as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.77 (s, 3H), 2.65-2.76 (m, 2H), 2.43-2.54 (m, 2H), 1.77-1.88 (m, 2H), 1.59-1.76 (m, 4H). Also isolated 200 mg (32%) of the less polar 3-iodo-2-methyl-2,4,5,6,7,8-hexahydrocycloheptapyrazole as a white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.84 (s, 3H), 2.70-2.79 (m, 2H), 2.42-2.51 (m, 2H), 1.77-1.88 (m, 2H), 1.57-1.73 (m, 4H).

1. stirringStirring
2. waitwas continued at 0° C. for 30 min
3. waitat room temperature for 2 h
4. customThe reaction was quenched with water
5. extractionextracted with EtOAc (2×)
6. dry with materialThe organics were dried over MgSO4
7. concentrationconcentrated
8. customThe residue was absorbed on SiO2
9. customchromatographed with 10% to 20% EtOAc/hexanes

ORD record

ord-5e9705ea15d845a5975873e7f4965dc5

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2