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. BH3THF (1M 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-14cfc85a2f814e30bcdeb47c7e502bb0

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592467B2