Hydrogen Peroxide → [3-(6-Bromo-benzothiazol-2-yl)-cyclobutyl]-methanol

Temperature

0 °C

The product of Example 1B (600.0 mg, 2.14 mmole) was dissolved in 4 ml of THF and cooled to 0° C. BH3.THF (1 M in THF, 5.35 ml, 5.35 mmole) was added to it and the mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was cooled to 0° C., 30% H2O2 (2.5 ml) and 3M NaOH were successively added dropwise. The mixture was slowly warmed to room temperature and stirred for 5 hours. The mixture was quenched with brine, and extracted three times with dichloromethane. The combined organics were washed with sodium bisulfite and brine, dried over sodium sulfate, filtered and concentrated to the crude product, which was purified by chromatography (5% methanol in dichloromethane) to provide the title compound (268.9 mg, 42.1%). 1H NMR (300 MHz, CDCl3) 7.98 (d, J=2.0 Hz, 1H) 7.83 (d, J=8.8 Hz, 1H) 7.56 (dd, J=8.7, 1.9 Hz, 1H) 3.79 (m, 2H) 3.66 (m, 1H) 2.55-2.70 (m, 3H) 2.42 (m, 1H) 2.26 (m, 1H). MS: (M+H)+=298/300.

1. temperatureto warm to room temperature
2. temperatureThe mixture was cooled to 0° C.
3. temperatureThe mixture was slowly warmed to room temperature
4. stirringstirred for 5 hours
5. customThe mixture was quenched with brine
6. extractionextracted three times with dichloromethane
7. washThe combined organics were washed with sodium bisulfite and brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated to the crude product, which
11. customwas purified by chromatography (5% methanol in dichloromethane)

ORD record

ord-18718eada723499fadd911f3829ac32d

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576110B2