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

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence